EP2668156B1 - Composition polymérisable comprenant un sulfonate d'oxime en tant qu'agent de durcissement thermique - Google Patents

Composition polymérisable comprenant un sulfonate d'oxime en tant qu'agent de durcissement thermique Download PDF

Info

Publication number
EP2668156B1
EP2668156B1 EP12701354.8A EP12701354A EP2668156B1 EP 2668156 B1 EP2668156 B1 EP 2668156B1 EP 12701354 A EP12701354 A EP 12701354A EP 2668156 B1 EP2668156 B1 EP 2668156B1
Authority
EP
European Patent Office
Prior art keywords
alkyl
radicals
cycloalkylene
interrupted
arylene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Not-in-force
Application number
EP12701354.8A
Other languages
German (de)
English (en)
Other versions
EP2668156A1 (fr
Inventor
Kazuhiko Kunimoto
Kaori Sameshima
Yuki Matsuoka
Hisatoshi Kura
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP12701354.8A priority Critical patent/EP2668156B1/fr
Publication of EP2668156A1 publication Critical patent/EP2668156A1/fr
Application granted granted Critical
Publication of EP2668156B1 publication Critical patent/EP2668156B1/fr
Not-in-force legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
    • C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/67—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/58—Derivatives of thiocarboxylic acids, the doubly-bound oxygen atoms being replaced by nitrogen atoms, e.g. imino-thio ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/60—Thiocarboxylic acids having sulfur atoms of thiocarboxyl groups further doubly-bound to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/59—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with at least one of the bonds being to sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/54—Nitrogen and either oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
    • C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers
    • G03F7/322—Aqueous alkaline compositions
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays

Definitions

  • the present invention relates to a polymerizable composition comprising at least one ethylenically unsaturated, polymerizable compound and at least one oxime sulfonate, to novel oxime sulfonates and to the use of the oxime sulfonates as thermal curing promoter. Furthermore, the present invention relates to the use of said composition.
  • color filters mainly for liquid crystal displays (LCD).
  • LCD liquid crystal displays
  • color filters for liquid crystal display which comprises black matrix and red, green and blue color pixels on a glass substrate, are manufactured by photolithography using radically photopolymerizable resists. After the photolithographic process, thermal curing is performed at about 230° C for 30 min to polymerize remaining acrylic double bonds to attain required durability in the production process of CF/LCD and for long-term survival in LCD as permanent coat.
  • An overcoat layer for LCD is used to planarize a surface of the color filter and enhance orientation of liquid crystal and to prevent ion elution from CF to the liquid crystal.
  • acrylic resins and/or epoxy resins or polyimide reins are usually employed as a base material for a colored coating film in a color filter.
  • the overcoat is usually manufactured by heating, for example, at about 220°C for 30 min or in combination with photolithoglaphy prior to the post-baking process. Thermal stability, light resistance, adhesiveness, hardness and transparency are required for the overcoat layer.
  • Spacer for LCD which controls a cell gap of the liquid crystal layer in LCD panels, is formed with high positional precision by photolithography using a photosensitive composition.
  • a photospacer is manufactured by photolithography using radically polymerizable resist on overcoat or color filter. After photolithography, the photospacer is baked, for example, at 220°C for 60 min to attain thermal stability, mechanical strength, adhesiveness, cell gap controllability and high deformation restorability.
  • a variety of curing compositions comprising a thermal curing promoter require long curing times and/or high curing temperatures. These high curing temperatures raise energy requirements and impose problems in coating substrates such as inexpensive soda-lime glass as substrate which is sensitive to the elevated temperatures. A high curing reactivity of the thermal curing promoter is also desirable from the viewpoint of productivity.
  • thermal curing promoter A large number of organic substances belonging to the classes of peroxides or azo compounds are known for the application as thermal curing promoter to attain low curing temperatures.
  • compositions comprising them often present difficulties concerning the storage stability and safety during transport due to their comparatively low decomposition temperature. Accordingly, there is a constant need for thermal curing promoters that meet the technical stability requirement.
  • the thermal curing promoter should allow the curing of low temperature curable compositions and the reduction of curing time.
  • the thermal curing promoter should show e.g. a good stability at the pre-baking process to remove the solvent prior to photolithography and enhancement of curing at an elevated temperature in the post-baking process after the photolithography.
  • Jpn, 1063-1070 (2003 ) the preparation of primary amines by the reaction of 1,3-dimethyl-2-imidazolidinone O-4-methylbenzenesulfonyloxime or 3-methyl-oxazolidin-2-one-O-4-methylbenzenesulfonyloxime with alkyl and aryl Grignard reagents. Described is also the synthesis of the amidoxime of the formula (1) by reacting N-methyl-2-oxazolidinone O-p-tosyloxime with phenylmagnesium bromide K. Akiba, H. Shiraishi and N. Inamoto describe in Bulletin of the Chemical Society of Japan, vol. 52, pp. 263-264 the reaction of the tosyloximino compound of the formula with Grignard reagents.
  • the compounds 4-phenylmethyl-O-tolylsulfonyl-2,3-thiomorpholinedione-2-oxime, 4-phenylmethyl-O-(fluorophenyl)sulfonyl-2,3-thiomorpholinedione-2-oxime and 4-phenylmethyl-O-phenylsulfonyl-2,3-thiomorpholinedione-2-oxime are known from Models in Chemistry 131 (3-4), pp. 529-534 . The use of these compounds as curing promoter is not described.
  • the compounds 4-phenylmethyl-O-tosyl-2,3-thiomorpholinedione-2-oxime, 4-phenylmethyl-O-phenylsulfonyl-2,3-thiomorpholinedione-2-oxime and 4-phenylmethyl-O-(4-fluorophenylsulfonyl)-2,3-thiomorpholinedione-2-oxime are known from WO 89/05805 . These compounds are effective against gastric and duodenal ulcers.
  • the compound alpha-phenylthio 3-(2-chloro-4-trifluoromethylphenoxy)-6-nitrobenzaldehyde O-methylsulfonyl oxime is known from EP 0174046 .
  • the compound can be used in combating undesired plant growth.
  • the compound [cyano(p-tolylsulfonyl)methylene]amino methanesulfonate is known from US 4,278,613 .
  • the compounds [1-[(6-chloro-3-pyridyl)methyl]pyrrolidin-2-ylidene]amino methanesulfonate; [1-[(6-chloro-3-pyridyl)methyl]pyrrolidin-2-ylidene]amino ethanesulfonate; and [1-[(6-chloro-3-pyridyl)methyl]pyrrolidin-2-ylidene]amino 4-methylbenzenesulfonate are known fromEP 2 522 666.
  • JP10010718 discloses a color former, which includes organic peroxides as thermal polymerization initiators and production of a color filter having good solvent resistance by applying post-baking process, preferably at 100 ⁇ 180°C, after photolithography process.
  • JP 2003330184 discloses a colored photosensitive resin composition capable of forming a color filter having high heat resistance, high hardness and high solvent resistance even after the resin composition is subjected to heat treatment of comparatively low temperature.
  • the resin is composed of a polymerization initiator having an oxadiazole structure or a triazine structure containing a trihalomethyl group.
  • JP 2003015288 discloses a radiation sensitive composition, including thermal polymerization initiators like organic peroxides, hydroperoxide and azo compounds, capable of forming a color filter having satisfactory adhesion to a plastics substrate even if such low temperature treatment as not to cause deformation or yellowing to the plastics substrate is adopted when the color filter is formed on the plastics substrate and to provide a color filter formed form the composition.
  • the radiation sensitive composition contains (A) a colorant, (B) an alkali-soluble resin, (C) a polyfunctional monomer, (D) a photopolymerization initiator and (E) a thermal polymerization initiator.
  • US 2008/014675 describes the polymerisation of a conjugated diene monomer in the presence of a lanthanide-based catalyst to form a pseudo-living polymer and reacting the pseudo-living polymer with a protected oxime compound to form a functionalized polymer.
  • the protected oxime compound can be an O-sulfonyloxime such as e.g. 1,3-dimethyl-2-imidazolidinone O-benzenesulfonyloxime.
  • US 2008/0146745 relates to polymers functionalized with protected oxime compounds and mentions the oxime compound Andre Le Berre et al. describe in Comptes Rendues des Seances de I' Académie des Sciences, Groupe B, 1964, 259 (1), 176-9 the reduction of pyrrolidin-2-one oxime tosylate and 1-methylpyrrolidin-2-one oxime tosylate.
  • US 4,123,255 relates to O-sulfonyl-alpha-cyano-2,6-dihalobenzaldoximes and their use as active pre-emergent herbicides.
  • the O-sulfonyl-alpha-cyano-2,6-dihalobenzaldoxime compounds are compared with O-methylsulfonyl-alpha-dimethylamino-2,6-dichlorobenzaldoxime with regard to their herbicidal activity.
  • the fungicidal sulfoneoxime esters of the formulae are known from WO 92/03050 .
  • the compound of the formula is known from the Ryan Scientific High Throughput Screening Compound Library, accession no. 0066990389
  • the compound of the formula is known from the Ryan Scientific High Throughput Screening Compound Library, accession no. 0067461735.
  • JP 2004026804 teaches the use of S-substituted oxime sulfonates, e.g. 1,2-bis(butylsulfonyloximino)-1,2-bis(methylthio)ethane, 1,2-bis(benzylsulfonyloximino)-1,2-bis(methylthio)ethane, R 1 : benzyl or n-butyl or R 2 : benzyl, n-propyl or n-butyl as photoacid generator in radiation-sensitive resin composition.
  • S-substituted oxime sulfonates e.g. 1,2-bis(butylsulfonyloximino)-1,2-bis(methylthio)ethane, 1,2-bis(benzylsulfonyloximino)-1,2-bis(methylthio)ethane, R 1 : benzyl or n-butyl or R 2 : benzyl, n-
  • the present invention is based on the object, therefore, of providing a curing promoter having a good curing performance.
  • the invention relates to a polymerizable composition
  • a polymerizable composition comprising
  • the invention also relates to compounds of the formula I as defined above, wherein R 1 is not substituted heterocycloalkyl.
  • a further aspect of the invention relates to the use of a composition as defined above for the production of color filters for display applications, spacers for LCD, overcoat layer for color filter and LCD, sealant for LCD, optical films for a variety of display applications, anisotropy conducting adhesive for LCD, insulation layer for LCD, to generate structures or layers in the manufacturing processes of plasma-display panels, electroluminescence displays and LCD, to manufacture solder mask, dielectric layers in a sequential build-up layer of a printed circuit board.
  • a further aspect of the invention relates to a coated substrate which is coated on at least one surface with a composition as defined above.
  • a further aspect of the invention relates to a color filter prepared by providing red, green and blue picture elements and a black matrix, all comprising a photosensitive resin and a pigment on a transparent substrate and providing a transparent electrode either on the surface of the substrate or on the surface of the color filter layer, wherein said photosensitive resin comprises a polyfunctional acrylate monomer, an organic polymer binder, a photopolymerization initiator and an oxime sulfonate compound of the formula I as defined above as thermal curing promoter.
  • the compounds of the general formula I are characterized in that at least one heteroatom selected from S and N is attached to the oxime carbon atom.
  • the compounds of the general formula I have at least one of the following advantageous properties:
  • halogen denotes in each case fluorine, bromine, chlorine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • halogen denotes fluorine, chlorine, bromine or iodine, particularly fluorine or chlorine.
  • alkyl refers to saturated straight-chain or branched hydrocarbon radicals having usually 1 to 4, to 6, to 8, to 12, to 16 or to 30 carbon atoms. Alkyl is preferably C 1 -C 12 -alkyl and more preferably C 1 -C 8 -alkyl.
  • alkyl groups are especially methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neo-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-hexadecyl, n-octadecyl and n-eicosyl.
  • Alkyl interrupted by CO, and/or heteroatoms such as -O-, -S- and -N(R 6 )- is for example interrupted once or more times, e.g. 1, 2, 3, 4, 5, 6, 7, 8 or 9, or once or twice. If alkyl is interrupted, for example once, twice, three or four times by CO, and/or heteroatoms such as -O-, -S- and -N(R 6 )-, at least one internal methylene group of alkyl is replaced by C(O), -O-, -S- or -N(R 6 )-, i.e. -O-, -S-, -N(R 6 )- and CO are not located at the termini of the alkyl group.
  • R 6 is as defined above. If a plurality of O, S or NR 6 occurs, they are usually non-adjacent, i.e. they are separated from one another by at least one methylene group. If a plurality of those interrupting heteroatoms selected from O, S or NR 6 occurs in alkyl, those heteroatoms are usually identical.
  • alkyl interrupted by 1 oxygen atom may also be referred to as alkoxy-alkyl or alkyl interrupted by 2 oxygen atoms may also be referred to as alkoxy-alkoxy-alkyl.
  • alkyl interrupted by 1 sulfur atom may also be referred to as alkyl-S-alkyl (alkylsulfanyl-alkyl) or, alkyl interrupted by 2 sulfur atoms may also be referred to as alkyl-S-alkyl-S-alkyl (alkylsulfanyl-alkylsulfanyl-alkyl).
  • Substituted alkyl groups may, depending on the length of the alkyl chain, have one or more (e.g. 1, 2, 3, 4, 5, 6, 7, 8 or more than 9) identical or different substituents.
  • alkyl substituted by cycloalkyl where cycloalkyl is interrupted by one CO group and carries one or more alkyl groups is camphoryl, especially camphor-10-yl where * is the point of attachment to the remainder of the molecule.
  • haloalkyl as used herein, which is also expressed as “alkyl which may be substituted by halogen”, refers to straight-chain or branched hydrocarbon radicals (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • haloalkyl examples are C 1 -C 20 -fluoroalkyl, especially C 1 -C 6 -fluoroalkyl, C 1 -C 20 chloroalkyl, especially C 1 -C 6 -chloroalkyl and C 1 -C 20 -bromoalkyl, especially C 1 -C 6 -bromoalkyl such as chloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2,-trifluoroethyl and 2-bromopropyl.
  • alkoxy refers to a saturated straight-chain or branched, alkyl radical having usually 1 to 4, to 6, to 8, to 12, to 16 or to 20 carbon atoms which is attached via an oxygen atom to the remainder of the molecule.
  • Examples are methoxy, ethoxy, propoxy, isopropoxy, n-butyloxy, sec-butyloxy, iso-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, 2,4,4-trimethylpentyloxy, 2-ethylhexyloxy, octyloxy, nonyloxy, decyloxy, dodecyloxy, hexadecyloxy, octadecyloxy or icosyloxy, in particular methoxy, ethoxy, propoxy, isopropoxy, n-butyloxy, sec-butyloxy, iso-butyloxy, tert-butyloxy, especially methoxy.
  • phenylalkoxy refers to phenyl, which is bound via an alkoxy group having preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, to the remainder of the molecule, examples including phenoxymethyl, 1-phenoxyethyl, 2-phenoxyethyl, and the like.
  • alkylsulfanyl refers to a saturated straight-chain or branched, alkyl radical having usually 1 to 4, to 6, to 8, to 12, to 16 or to 20 carbon atoms as defined above which is attached via a sulfur atom to the remainder of the molecule. Examples are methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, sec-butylsulfanyl, isobutylsulfanyl and tert-butylsulfanyl.
  • C 1 -C 20 -alkanoyl refers to formyl and a saturated straight-chain or branched alkyl radical having 1 to 19 carbon atoms attached through the carbon atom of the carbonyl group at any position in the alkyl group, for example acetyl, propanoyl, 2-methyl-propanoyl, butanoyl, pentanoyl, hexanoyl.
  • C 1 -C 6 -alkoxycarbonyl (C 1 -C 6 -alkyl-O-C(O)-) as used herein refers to a saturated straight-chain or branched alkoxy radical having 1 to 6 carbon atoms as defined above attached through the carbon atom of the carbonyl group to the remainder of the molecule. Examples are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl or pentoxycarbonyl.
  • alkenyl refers to mono- or polyunsaturated, straight-chain or branched hydrocarbon radicals having usually 2 to 30, preferably 2 to 20, more preferably 2 to 10 carbon atoms, having one or more, e.g.
  • 1, 2, 3 or more than two double bonds e.g., C 2 -C 6 -alkenyl having one double bond such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, or alkadienyl having usually 4 to 10 carbon atoms and two double bonds in any position, for example 1,3-butadienyl, 1,3-pentadienyl, hexa-1,4-dien-1-yl, hexa-1,4-dien-3-yl, hexa-1,4-dien-6-yl, hepta-1,4-dien-7-yl, hepta-1,5-dien-1-yl and the like.
  • Alkenyl interrupted by CO, and/or heteroatoms such as -O-, -S- or -N(R 6 )- is for example interrupted once or more times, e.g. 1, 2, 3, 4, 5, 6, 7, 8 or 9, or once or twice. If alkenyl is interrupted by CO, and/or heteroatoms such as -O-, -S- and -N(R 6 )-, at least one internal methylene group of alkenyl is replaced by C(O), -O-, -S- or -N(R 6 )-, i.e. -O-, -S-, -N(R 6 )- and CO are not located at the termini of the alkenyl group.
  • R 6 is as defined above.
  • O, S or NR 6 are usually non-adjacent, i.e. they are separated from one another by at least one methylene group). If a plurality of those interrupting heteroatoms selected from O, S or NR 6 occurs in alkenyl, those heteroatoms are usually identical.
  • Substituted alkenyl groups may, depending on the length of the alkenyl chain, have one or more (e.g. 1, 2, 3, 4, 5, 6, 7, 8 or more than 8) identical or different substituents.
  • haloalkenyl as used herein, which is also expressed as “alkenyl which may be substituted by halogen”, refers to unsaturated straight-chain or branched hydrocarbon radicals having one or more double bonds (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • haloalkenyl are C 2 -C 20 -fluoroalkenyl, C 2 -C 20 chloroalkenyl and C 2 -C 20 -bromoalkenyl.
  • C 3 -C 6 -alkenoxy refers to a mono- or diunsaturated straight-chain or branched alkenyl radical having 3 to 6 carbon atoms as defined above linked via an oxygen atom to the remainder of the molecule.
  • Examples are vinyloxy, 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propenyloxy, 2-methyl-1-propenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 1-pentenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-1-butenyloxy, 2-methyl-1-butenyloxy, 3-methyl-1-butenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyloxy, 1,2-dimethyl-1-propenyloxy, 1,2-dimethyl-2-propenyloxy, 1-ethyl-1-prop
  • C 3 -C 6 -alkenoyl (C 2 -C 5 -alkenyl-C(O)-)" as used herein refers to a mono- or diunsaturated straight-chain or branched alkenyl radical having 2 to 5 carbon atoms as defined above attached through the carbon atom of the carbonyl group at any position in the alkenyl group, for example propenoyl, 2-methyl-propenoyl, butenoyl, pentenoyl, 1,3-pentadienoyl, 5-hexenoyl.
  • alkynyl refers to unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 30, preferably 2 to 20, more preferably 2 to 10 carbon atoms and one or more, e.g. two, three or four triple bonds, e.g.
  • ethynyl propargyl (2-propyn-1-yl), 1-propyn-1-yl, 1-methylprop-2-yn-1-yl), 2-butyn-1-yl, 3-butyn-1-yl, 1-pentyn-1-yl, 3-pentyn-1-yl, 4-pentyn-1-yl, 1-methylbut-2-yn-1-yl, 1-ethylprop-2-yn-1-yl and the like.
  • Alkynyl interrupted by CO, and/or heteroatoms such as -O-, -S- and -N(R 6 )- is for example interrupted once or more times, e.g. 1, 2, 3, 4, 5, 6, 7, 8 or 9, or once or twice. If alkynyl is interrupted by CO and/or heteroatoms such as -O-, -S- and -N(R 6 )-, at least one internal methylene group of alkynyl is replaced by C(O) -O-, -S- and -N(R 6 )-, i.e. -O-, -S-, -N(R 6 )- and CO are not located at the termini of the alkynyl group.
  • R 6 is as defined above. If a plurality of O, S or NR 6 occurs, they are usually non-adjacent, i.e. they are separated from one another by at least one methylene group. If a plurality of those interrupting heteroatoms selected from O, S or NR 6 occurs in alkynyl, those heteroatoms are usually identical.
  • Substituted alkynyl groups may, depending on the length of the alkynyl chain, have one or more (e.g. 1, 2, 3, 4, 5 or more than 5) identical or different substituents.
  • haloalkynyl as used herein, which is also expressed as “alkynyl which may be substituted by halogen”, refers to unsaturated straight-chain or branched hydrocarbon radicals having one or more triple bonds (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • haloalkynyl are C 2 -C 20 -fluoroalkynyl, C 2 -C 20 chloroalkynyl and C 2 -C 20 -bromoalkynyl.
  • C 3 -C 6 -alkynyloxy refers to a mono- or diunsaturated straight-chain or branched alkynyl radical having 3 to 6 carbon atoms as defined above which is attached via an oxygen atom to the remainder of the molecule, for example 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-2-butynyloxy, 1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-hexynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy and 1-methyl-3-pentynyloxy.
  • cycloalkyl refers to a mono- or polycyclic, e.g. bi- or tricyclic aliphatic radical having usually from 3 to 30, preferably 3 to 20, more preferably 3 to 16, or 3 to 12 carbon atoms or in particular 3 to 8 carbon atoms.
  • monocyclic rings are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, especially cyclopentyl and cyclohexyl.
  • polycyclic rings are perhydroanthracyl, perhydronaphthyl, perhydrofluorenyl, perhydrochrysenyl, perhydropicenyl, adamantyl, bicyclo[1.1.1]pentyl, bicyclo[2.2.1]heptyl, bicyclo[4.2.2]decyl, bicyclo[2.2.2]octyl, bicyclo[3.3.0]octyl bicyclo[3.3.2]decyl, bicyclo[4.4.0]decyl, bicyclo[4.3.2] undecyl, bicyclo[4.3.3]dodecyl, bicyclo[3.3.3]undecyl, bicyclo[4.3.1]decyl, bicyclo[4.2.1]nonyl, bicyclo [3.3.1]nonyl, bicyclo[3.2.1]octyl and the like.
  • Cycloalkyl may be interrupted by one or more CO groups, usually one or two groups.
  • An example for cycloalkyl interrupted by 1 CO group is 3-oxobicyclo[2.2.1]heptyl.
  • cycloalkyl is substituted by one or more identical or different radicals, it is for example mono-, di-, tri-, tetra- or pentasubstituted, e.g. by C 1 -C 4 -alkyl.
  • cycloalkyl is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted.
  • heterocyclyl (also referred to as heterocycloalkyl) as used herein includes in general 3-, 4-, 5-, 6-, 7- or 8- membered, in particular 5-, 6-, 7- or 8-membered monocyclic heterocyclic non-aromatic radicals and 8 to 10 membered bicyclic heterocyclic non-aromatic radicals, the mono- and bicyclic non-aromatic radicals may be saturated or unsaturated.
  • the mono- and bicyclic heterocyclic non-aromatic radicals usually comprise 1, 2, 3 or 4 heteroatoms, in particular 1 or 2 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO 2 .
  • Heterocycloalkyl may be interrupted by one or more CO groups, usually one or two groups.
  • heterocyclyl When heterocyclyl is substituted by one or more identical or different radicals, it is for example mono-, di-, tri-, tetra- or pentasubstituted.
  • saturated or unsaturated 3-, 4-, 5-, 6-, 7- or 8-membered heterocyclic radicals comprise saturated or unsaturated, non-aromatic heterocyclic rings, such as oxiranyl, oxetanyl, thietanyl, thietanyl-S-oxid (S-oxothietanyl), thietanyl-S-dioxid (S-dioxothiethanyl), pyrrolidinyl, pyrazolinyl, imidazolinyl, pyrrolinyl, pyrazolinyl, imidazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, dioxolenyl, thiolanyl, S-oxothiolanyl, S-dioxothiolanyl, dihydrothienyl, S-oxodihydrothienyl, S-
  • heterocyclyl is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted.
  • aryl refers to a monovalent aromatic group having 6 to 20 ring carbon atoms.
  • the term aryl includes a monocyclic radical, such as phenyl, or polycyclic, e.g. bi-, tri- or tetracyclic radicals, for example naphthyl, phenanthrenyl or anthracenyl. Preferred examples for aryl are phenyl and naphthyl. Substituted phenyl is substituted once, twice, three times, four times or five times.
  • Polycylic radicals aryl are usually substituted by 1, 2, 3, 4, 5, 6, 7 or 8 substituents, preferably 1, 2, 3 or 4.
  • heteroaryl (also referred to as “hetaryl”) includes in general 5- or 6-membered unsaturated monocyclic heterocyclic radicals and 8 to 10 membered unsaturated bicyclic heterocyclic radicals which are aromatic, i.e. they comply with Hückel's rule (4n+2 rule). Hetaryl usually comprise besides carbon atom(s) as ring member(s) 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring members.
  • Examples of 5- or 6-membered heteroaromatic radicals include: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isoxazolyl, 4- isoxazolyl or 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl or 5-isothiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 2- or 5-[1,3,4]oxadiazolyl, 4- or 5-(1,2,3-oxadiazol)yl, 3- or 5-(1,2,4-oxadiazol)yl, 2- or 5-(1,3,4-thiadiazol)yl, 2- or 5-(
  • heteroaryl also includes bicyclic 8- to 10-membered heteroaromatic radicals comprising as ring members 1,2 or 3 heteroatoms selected from N, O and S, wherein a 5- or 6-membered heteroaromatic ring is fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical.
  • Examples of a 5- or 6-membered heteroaromatic ring fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical include benzofuranyl, benzothienyl, indolyl, indazolyl, benzimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, isochinolinyl, purinyl, 1,8-naphthyridyl, pteridyl, pyrido[3,2-d]pyrimidyl or pyridoimidazolyl and the like.
  • These fused hetaryl radicals may be bonded to the remainder of the molecule via any ring atom of 5- or 6-membered heteroaromatic ring or via a carbon atom of the fused phenyl moiety.
  • heteroaryl is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted.
  • C 1 -C 30 -alkylene (or alkanediyl) as used herein in each case denotes an alkyl radical having 1 to 30 carbon atoms as defined above, wherein one hydrogen atom at any position of the alkyl radical is replaced by one further binding site, thus forming a bivalent radical.
  • C 1 -C 20 -alkylene is a divalent branched or unbranched saturated aliphatic chain having 1 to 20 carbon atoms, for example -CH 2 -, -CH 2 CH 2 -, -CH(CH 3 )-, -CH 2 CH 2 CH 2 -, -CH(CH 3 )CH 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH(CH 3 )CH 2 -, -CH(CH 3 )CH(CH 3 )-, -CH 2 CH 2 CH 2 CH 2 CH 2 -, -CH 2 (CH 2 ) 2 CH(CH 3 )-, -CH 2 C(CH 3 ) 2 CH 2 -, and the like.
  • each alkylene may be interrupted by one or more identical or different groups selected from -O-, -S-, -N(R 6 )- and CO" denotes an alkylene chain having usually 1 to 20 carbon atoms as defined above where at least one internal methylene group of the alkylene chain is replaced by O-, -S-, -N(R 6 )- or CO.
  • the alkylene moiety may comprise, e.g. 1, 2, 3, 4, 5, or more than 5 identical or different groups selected from O, S, NR 6 and CO.
  • R 6 is as defined above. If a plurality of CO, O, S or NR 6 occurs, they are usually non-adjacent, i.e. they are separated from one another by at least one methylene group. If a plurality of those interrupting heteroatoms selected from O, S or NR 6 occurs in alkylene, those heteroatoms are usually identical.
  • radical alkylene is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted.
  • alkenylene (or alkenediyl) as used herein in each case denotes a straight-chain or branched alkenyl radical having usually 2 to 30, preferably 2 to 20 carbon atoms as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • C 2 -C 20 -alkenylene is a divalent straight-chain or branched aliphatic chain having 2 to 20 carbon atoms, for example vinylene, propenylene, but-1-enylene, but-2-enylene, penta-1,3-dienylene, and the like.
  • each alkenylene may be interrupted by one or more identical or different groups selected from -O-, -S-, -N(R 6 )- and CO" denotes an alkenylene chain having usually 2 to 30, preferably 2 to 20 carbon atoms as defined above where at least one internal methylene group of the alkenylene chain is replaced by O-, -S-, -N(R 6 )- or CO.
  • the alkenylene moiety may comprise, e.g. 1, 2, 3, 4, 5, or more than 5 identical or different groups selected from O, S, NR 6 and CO.
  • R 6 is as defined above. If a plurality of O, S or NR 6 occurs, they are usually non-adjacent, i.e. they are separated from one another by at least one methylene group. If a plurality of those interrupting heteroatoms selected from O, S or NR 6 occurs in alkenylene, those heteroatoms are usually identical.
  • radical alkenylene is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted.
  • C 2 -C 30 -alkynylene (or alkynediyl) as used herein in each case denotes a straight-chain or branched alkynyl radical having 2 to 30 carbon atoms as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • C 2 -C 20 -alkynylene is a divalent straight-chain or branched aliphatic chain having 2 to 20 carbon atoms.
  • each alkynylene may be interrupted by one or more identical or different groups selected from -O-, -S-, -N(R 6 )- and CO" denotes an alkynylene chain having usually 2 to 30, preferably 2 to 20 carbon atoms as defined above where at least one internal methylene group of the alkynylene chain is replaced by O-, -S-, -N(R 6 )- or CO.
  • the alkynylene moiety may comprise, e.g. 1, 2, 3, 4, 5, or more than 5 identical or different groups selected from O, S, NR 6 and CO.
  • R 6 is as defined above. If a plurality of O, S or NR 6 occurs, they are usually non-adjacent, i.e. they are separated from one another by at least one methylene group. If a plurality of those interrupting heteroatoms selected from O, S or NR 6 occurs in alkynylene, those heteroatoms are usually identical.
  • radical alkynylene is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra-, penta-, hexa-, hepta- or octasubstituted or more than octasubstituted.
  • C 1 -C 30 -alkanetriyl denotes an alkanediyl radical having 1 to 30 carbon atoms as defined above, wherein one hydrogen atom at any position of the alkanediyl is replaced by one further binding site, thus forming a trivalent radical.
  • C 1 -C 20 -alkanetriyl is a trivalent branched or unbranched saturated aliphatic chain having 1 to 20 carbon atoms. If alkanetriyl is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted.
  • C 1 -C 30 -alkanetriyl which may be interrupted by one or more identical or different groups L 17 denotes an alkanetriyl chain having 1 to 30, preferably 1 to 20 carbon atoms as defined above where at least one internal methylene group of the alkynylene chain is replaced by a group L 17 .
  • the alkanetriyl chain moiety may comprise, e.g. 1, 2, 3, 4, 5, or more than 5 identical or different groups L 17 . If a plurality of O or S as interupting groups L 17 occurs, they are usually non-adjacent, i.e. they are separated from one another by at least one methylene group.
  • C 2 -C 30 -alkenetriyl denotes an alkenediyl radical having 2 to 30 carbon atoms as defined above, wherein one hydrogen atom at any position of the alkenediyl is replaced by one further binding site, thus forming a trivalent radical.
  • C 2 -C 20 -alkenetriyl is a trivalent branched or unbranched unsaturated aliphatic chain having 2 to 20 carbon atoms. If alkenetriyl is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted.
  • C 1 -C 30 -alkanetetrayl denotes an alkanetriyl radical having 1 to 30 carbon atoms as defined above, wherein one hydrogen atom at any position of the alkanetriyl is replaced by one further binding site, thus forming a tetravalent radical.
  • C 1 -C 30 -alkanetetrayl is a tetravalent branched or unbranched saturated aliphatic chain having 1 to 30 carbon atoms. If alkanetetrayl is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted.
  • C 2 -C 30 -alkanehexayl denotes an alkanetetrayl radical having 2 to 30 carbon atoms, wherein 2 hydrogen atoms at any position of the alkanetetrayl are replaced by two further binding site, thus forming a hexavalent radical.
  • C 2 -C 30 -alkanehexayl is a hexavalent branched or unbranched saturated aliphatic chain having 2 to 30 carbon atom. If alkanehexayl is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted.
  • C 3 -C 16 -cycloalkanediyl (also referred to as cycloalkylene) refers to cycloalkyl radical having 3 to 16 carbon atoms as defined above, wherein one hydrogen atom at any position of cycloalkyl is replaced by one further binding site, thus forming a divalent radical.
  • the bonding sites are either situated in the same ring or in different rings. Examples of monocyclic rings are cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene or cycloheptylen, especially cyclohexylene.
  • polycyclic rings are perhydroanthracylene, perhydronaphthylene, perhydrofluorenylene, perhydrochrysenylene, perhydropicenylene, adamantylene, bicyclo[1.1.1]pentylen, bicycle[2.2.1]heptylene, bicyclo[4.2.2]decylene, bicycle-[2.2.2]octylene, bicyclo[3.3.2]decylene, bicyclo[4.3.2]undecylene, bicyclo[4.3.3]dodecylene, bicyclo[3.3.3]undecylene, bicyclo[4.3.1]decylene, bicyclo[4.2.1]nonylene, bicyclo[3.3.1]nonylene, bicyclo[3.2.1]octylene and the like.
  • cycloalkanediyl is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted, e.g. by C 1 -C 4 -alkyl.
  • C 3 -C 16 -cycloalkanetriyl refers to cycloalkenyl radical having 3 to 16 carbon atoms as defined above, wherein one hydrogen atom at any position of the cycloalkanediyl is replaced by one further binding site, thus forming a trivalent radical.
  • the bonding sites are either situated in the same ring or in different rings. If cycloalkanetriyl is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted
  • C 6 -C 20 -arylene (also referred to as arenediyl) as used herein refers to an aryl group as defined above, wherein one hydrogen atom at any position of the aryl group is replaced by one further binding site, thus forming a bivalent radical.
  • the bonding sites are either situated in the same ring or in different rings.
  • arylene are phenylen, naphthylene, anthracenediyl or phenanthrenediyl. If arylene is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted.
  • phenylene refers to 1,2-phenylene (o-phenylene or 1,2-benzenediyl), 1,3-phenylene (m-phenylene, 1,3-benzenediyl) and 1,4-phenylene (p-phenylene or 1,4-benzenediyl).
  • naphthylene refers to 1,2-naphthylene, 1,3-naphthylene, 1,4-naphthylene, 1,5-naphthylene, 1,8-naphthylene, 2,3-naphthylene and 2,7-naphthylene.
  • xylylene refers to 1,2-xylylene (1,2-methylenephenylenemethylene, 1,2-CH 2 -C 6 H 4 -CH 2 ), 1,3-xylylene (1,3-methylenephenylenemethylene, 1,3-CH 2 -C 6 H 4 -CH 2 ) and 1,4-xylylene (1,4-methylenephenylenemethylene, 1,4-CH 2 -C 6 H 4 -CH 2 ).
  • arenetriyl refers to an arylene group as defined above, wherein one hydrogen atom at any position of the arylene group is replaced by one further binding site, thus forming a trivalent radical.
  • the bonding sites are either situated in the same ring or in different rings.
  • arenetriyl are 1,2,4-benzenetriyl, 1,3,5-benzenetriyl, 1,3,5-naphthalenetriyl, 1,4,5-naphthalenediyl, anthracenetriyl or phenanthrenetriyl. If arenetriyl is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted.
  • heteroaryl refers to a heteroaryl radical as defined above, where one hydrogen atom at any position of the heteroaryl group is replaced by a further binding site, thus forming a divalent radical.
  • the bonding sites are either situated in the same ring or in different rings.
  • Heteroarenediyl can be C-attached or N-attached where such is possible.
  • a pyrrolediyl, imidiazolediyl or pyrazolediyl can be N-attached or C-attached.
  • heteroarenediyl examples include pyridinediyl, pyrimidinediyl, pyridazinediyl, 1,2,3-triazinediyl, 1,2,4-triazinediyl, 1,2,3,4-tetrazinediyl, furandiyl, thiophenediyl, pyrrolediyl, thiazolediyl, thiadiazolediyl, pyrazolediyl, imidazolediyl, triazolediyl, oxazolediyl, isoxazolediyl, isothiazolediyl, oxadiazolediyl and the like. If heteroarenediyl is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted.
  • heteroarenetriyl refers to a heteroarenediyl as defined above, wherein one hydrogen atom at any position of the heteroarenediyl is replaced by one further binding site, thus forming a trivalent radical.
  • the bonding sites are either situated in the same ring or in different rings. If heteroarenetriyl is substituted by one or more substituents, it is, for example, mono-, di-, tri-, tetra- or pentasubstituted or more than pentasubstituted.
  • C n -C m -alkoxy-C 0 -C p -alkyl refers to an alkoxy group, as defined above, having n to m carbon atoms, which is bound to the remainder of the molecule via an alkylene group, as defined above, having o to p carbon atoms. Examples thereof are CH 2 -OCH 3 , CH 2 -OC 2 H 5 , n-propoxymethyl, CH 2 -OCH(CH 3 ) 2 , n-butoxymethyl.
  • C k -C l -alkoxy-C n- C m -alkoxy-C 0 -C p -alkyl refers to an alkoxy group, as defined above, having k to l carbon atoms, which is bound to the remainder of the molecule via a C n- C m -alkoxy-C 0 -C p -alkyl group, as defined above.
  • hydroxy-C n- C m -alkoxy-carbonyl refers to an alkoxy group carrying usually one hydroxy group and having n to m carbon atoms, which is bound to the remainder of the molecule via a carbonyl group.
  • C n -C n -alkoxycarbonyl-C o -C p -alkyl refers to an alkoxy radical having n to m carbon atoms which is attached through the carbon atom of the carbonyl group to an alkylene group, as defined above, having o to p carbon atoms.
  • Examples are C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl such as methoxycarbonylmethyl, ethoxycarbonylmethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 3-methoxycarbonylpropyl, 3-ethoxycarbonylpropyl, 4-methoxycarbonylbutyl or 4-ethoxycarbonylbutyl.
  • arylalkyl (also referred to as aryl-alkylene) as used herein refers to an aryl radical as defined above which is linked via an alkylene group, in particular via a methylene, 1,1-ethylene or 1,2-ethylene group, e.g. benzyl, 1-phenylethyl or 2-phenylethyl..
  • C n -C m -cycloalkyl-C o -C p -alkyl refers to a cycloalkyl group, as defined above, having n to m carbon atoms, which is bound to the remainder of the molecule via an alkylene group, as defined above, having o to p carbon atoms.
  • Examples are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cycloppentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, and the like.
  • heterocycloalkyl-C o -C p -alkyl refers to a heterocycloalkyl group, as defined above, which is bound to the remainder of the molecule via an alkylene group, as defined above, having o to p carbon atoms. Examples are hetarylmethyl, 1-hetarylethyl or 2-hetarylethyl.
  • substituents R 4 and R 5 are attached to a phenyl or naphthyl ring, they may also be phenyl or naphthyl which forms a 5- or 6-membered ring with the phenyl ring to which the SR 4 or OR 5 is attached via a direct bond, C 1 -C 4 -alkylene, O, S, NR 6 or CO.
  • # denotes the point of attachment and R 6 is as defined above.
  • R 6 and R 7 , R 10 and R 11 and/or R 12 and R 13 together with the N atom to which they are attached, may form a 5-, 6-, or 7-membered ring which optionally has a further heteroatom or heteroatomic group selected from CO, O, S or N(C 1 -C 8 -alkyl) as ring members and which may carry 1, 2, 3 or 4 C 1 -C 4 -alkyl.
  • Examples are morpholine, pyrrole, pyrrolidine, imidazolidine, piperidine or piperazine, preferably morpholine, piperidine or piperazine.
  • the term "b is 2 or b is 3 and -X-R 1 is bound to a carbon atom or nitrogen atom of Q via a divalent bridging group having 1 to 10 atoms between the flanking bonds ", examples fornthe divalent bridging group are X-(C 1 -C 6 -alkylene)-Y', X-(C 3 -C 6 -cycloalkylene)-Y', X-(heterocycloalkylene)-Y', X-(C 2 -C 6 -alkenylene)-Y', X-(o-phenylene)-Y', X-(o-xylylene)-Y', X-(o-phenylene-C 1 -C 4 -alkylene)-Y', X-(C 1 -C 4 -alkylene-o-phenylene)-Y' or S-C(S)-N(R 12 )-CO.
  • Each alkylene and alkenylene may be interrupted by one or more, e.g. 1 or 2, O, S, NR 12 or CO and/or may be substituted by one or more, e.g. 1, 2, 3, 4 or more than 4, F, Cl, Br, I, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 6 -C 10 -aryl, heteroaryl or C 6 -C 10 -aryl which issubstituted by one or more C 1 -C 12 -alkyl, C 1 -C 4 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 or CONR 10 R 11 ; cycloalkylene and heterocycloalkylene may be interrupted by one or more, e.g.
  • 1 or 2 CO and/or may be substituted by one or more e.g. 1, 2, 3, 4 or more than 4, C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, F, Cl, Br, I, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 6 -C 10 -aryl, heteroaryl or C 6 -C 10 -aryl which is substituted by one or more C 1 -C 12 -alkyl, C 1 -C 4 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 or CONR 10 R 11 , and each phenylene may be substituted by one or more e.g.
  • the divalent bridging group is preferably selected from phenylene and C 1 -C 6 -alkylene, where the last-mentioned radical may be interrupted by one or more, e.g. 1,2 or 3, identical or different groups selected from O, S, N(C 1 -C 8 -alkyl) and CO.
  • the term "at least" is meant to define one or more than one, for example one, two, three, preferably one to two.
  • one or more identical or different radicals is meant to define one, two, three, four, five, six, seven, eight or more than eight identical or different radicals.
  • the substituents Q, X, R 1 , R 2 and R 3 and the indices a, b and c independently of one another and preferably in combination have the meanings given below.
  • a preferred embodiment of the invention relates to compositions, compounds, methods and uses, wherein a in formula I is 0, 1, 2, 3, 4 or 6, in particular 0, 1, 2 or 3. According to a further particular aspect of this embodiment, a is 4.
  • a further preferred embodiment of the invention relates to compositions, compounds, methods and uses, wherein b in formula I is preferably 0 or 2.
  • a further preferred embodiment of the invention relates to compositions, compounds, methods and uses, wherein c in formula I is preferably 0 or 2. According to a further particular aspect of this embodiment c is 1.
  • a further preferred embodiment of the invention relates to compositions, compounds, methods and uses, wherein X in formula I is S or NR 14 . According to a particular aspect of this embodiment, X is S.
  • X is a radical NR 14 .
  • R 14 is preferably selected from C 1 -C 12 -alkyl, which may be interrupted by one or more, e.g. 1, 2 or 3, identical or different O, S, NR 6 or CO and/or may be substituted by one or more, e.g.
  • radicals R 14a selected from C 3 -C 8 -cycloalkyl, CN, COR 8 , COOR 9 , CONR 10 R 11 , phenyl, phenyl which is substituted by one, two, three, four or five radicals selected from C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 , and C 3 -C 8 -cycloalkyl which is interrupted by one or two CO groups and/or may be substituted by one, two, three, four or five radicals selected from C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, F, CI, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CO
  • R 14c selected from C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR5, NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 and phenyl; where R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 are as defined above and preferably have one of the preferred meanings.
  • R 14 is C 1 -C 12 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl-C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl or phenyl-C 1 -C 12 -alkyl, where the phenyl moiety of the last-mentioned radical is unsubstituted or substituted by one, two, three, four or five radicals selected from C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 .
  • R 14 is C 2 -C 6 -alkenyl.
  • R 14 is phenyl, which is unsubstituted or substituted by one, two, three, four or five identical or different radicals selected from C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, F, CI, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 and phenyl.
  • R 14 is C 1 -C 6 -alkyl, especially methyl, ethyl, n-propyl, isopropyl or n-butyl; benzyl; phenethyl; C 2 -C 6 -alkenyl especially allyl; C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl especially 2-methoxyethyl, 2-methoxypropyl, 2-ethoxyethyl or 2-ethoxypropyl; or C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, especially cyclopentylmethyl, cyclohexylmethyl, 2-cyclohexylethyl or 2-cyclopentylethyl.
  • Suitable examples for R 14 are methyl, ethyl, propyl, butyl, benzyl, phenethyl, allyl, 2-methoxyethyl, 3-methoxypropyl, cyclopentyl, cyclohexyl, cyclohexylmethyl or phenyl.
  • a further preferred embodiment of the invention relates to compositions, compounds, methods and uses, where in formula I two radicals R 14 together are a divalent bridging group having 1 to 20, preferably 1 to 10, atoms between the flanking bonds.
  • the divalent bridging group is preferably selected from C 1 -C 10 -alkylene, C 3 -C 12 -cycloalkylene, heterocycloalkylene, C 2 -C 10 -alkenylene, phenylene or naphthylene, where each alkylene and alkenylene may be interrupted by one or more, e.g. 1 or 2, O, S, N(H), N(C 1 -C 8 -alkyl) or CO and where cycloalkylene and heterocycloalkylene may be interrupted by one or more, e.g. 1 or 2 CO.
  • a further preferred embodiment of the invention relates to compositions, compounds, methods and uses, wherein R 1 in formula I is CSNR 12 R 13 ; C(O)R 9 ; CSOR 9 ; C 3 -C 12 -alkyl; C 2 -C 12 -alkenyl; C 3 -C 12 -cycloalkyl; C 1 -C 12 -alkyl, which is interrupted by one or more, e.g. 1, 2 or 3, identical or different groups selected from O, S, NR 6 or CO and/or which is substituted by one, two or three identical or different radicals R 1a ; C 2 -C 12 -alkenyl, which is interrupted by one or more, e.g.
  • R 1a is selected independently of one another from F, Cl, Br, I, CN, SR4, OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 3 -C 20 -cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, heteroaryl and C 6 -C 10 -aryl where the four last-mentioned radicals may carry one or more identical or different radicals R 1aa , where R 1aa is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 ;
  • R 1a is preferably SR 4 , COOR 9 , C 3 -C 8 -cycloalkyl, phenyl or 5- or 6-membered heteroaryl comprising besides carbon atoms 1 or 2 heteroatoms selected from N, O and S as ring members, where phenyl and heteroaryl may be unsubstituted or substituted by one, two, three, four or five identical or different radicals R 1aa .
  • R 1aa , R 4 and R 9 are as defined above.
  • R 4 is preferably phenyl-C 1 -C 4 -alkyl where the phenyl moiety may carry one or more identical or different radicals R 1aa .
  • phenyl-C 1 -C 4 -alkyl is benzyl or phenethyl.
  • R 9 is preferably C 1 -C 8 -alkyl which may be interrupted by 1 or 2 oxygen atoms and/or may carry a radical R 9a .
  • R 9a is preferably phenyl. Examples are methyl, ethyl, propy, butyl, 3-methoxybutyl or benzyl.
  • R 1a is C 1 -C 4 -alkoxycarbonyl, such as methoxycarbonyl or ethoxycarbonyl;C 1 -C 4 -alkoxy-C 1 -C 6 -alkoxycarbonyl such as 3-methoxybutoxycarbonyl; phenyl-C 1 -C 4 -alkylsulfanyl such as benzylsulfanyl or phenethylsulfanyl; 5- or 6-membered heteroaryl comprising besides carbon atoms 1 or 2 heteroatoms selected from O, S and N such as thiophen-2-yl, thiophen-3-yl, furan-2-yl or furan-3-yl, or C 3 -C 8 -cycloalkyl such as cyclopentyl, cyclohexyl or cycloheptyl.
  • C 1 -C 4 -alkoxycarbonyl such as methoxycarbonyl or ethoxycarbonyl
  • R 1a is 5- or 6-membered saturated heterocyclyl comprising besides carbon atoms one or two identical or different heteroatoms selected from O and S such as tetrahydrofuranyl, tetrahydrothienyl, tetrahydropyranyl or tetrahydrothiopyranyl.
  • R 1a is 4-cycanophenyl.
  • R 1b is preferably C 1 -C 6 -alkyl or C 2 -C 6 -alkenyl.
  • R 1c is preferably C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or nitro. Especially, R 1c is methyl, ethyl, propyl, allyl or nitro.
  • R 1d is preferably C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or nitro. Especially R 1d is C 2 -C 4 -alkenyl, in particular vinyl or allyl.
  • R 1 is C 1 -C 12 -alkyl which is interrupted by one or more, e.g. 1, 2 or 3 identical or different groups selected from O, S, NR 6 or CO and/or which is substituted by one, two or three identical or different radicals R 1a , it is preferably C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl; C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl; C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxycarbonyl-C 1 -C 3 -alkyl, especially C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxycarbonyl-C 1 -C 3 -alkyl; C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl; phenyl-C 1 -C 6 -alkyl; phenyl-C 1
  • R 1 is heteroaryl
  • R 1 is preferably 5- or 6-membered heteroaryl comprising besides carbon atoms 1 or 2 heteroatoms selected from N, O and S as ring members or 8-, 9- or 10-membered heteroaryl comprising as ring members 1, 2 or 3 heteroatoms selected from N, O and S.
  • Suitabe examples are pyridyl, thiazolyl, benzothiazolyl or benzoxazolyl. Further suitable examples are benzothiazolyl or benzofuranyl.
  • R 9 is preferably C 1 -C 20 -alkyl or C 1 -C 20 -alkyl in which the alkyl moiety is interrupted by one or more, e.g. 1, 2, 3, 4 or 5, non-adjacent oxygen atoms.
  • R 9 is preferably (CH 2 CH 2 O) x (C 1 -C 4 -alkyl) with x being 1, 2, 3, 4 or 5, in particular (CH 2 CH 2 O) x (C 1 -C 4 -alkyl) with x being 1, 2 or 3.
  • R 1 is heterocyclyl
  • R 1 is preferably 5- or 6-membered saturated or partially unsaturated heterocyclyl comprising besides carbon atoms one or two identical or different heteroatoms selected from N, NH and N(C 1 -C 8 -alkyl), such as morpholinyl, thiomorpholinyl, tetrahydrofuranyl, tetrahydrothienyl, 4,5-dihydrothienyl, tetrahydropyranyl or tetrahydrothiopyranyl.
  • R 1 is C 6 -C 10 -aroyl, which may be substituted by one or more identical or different radicals R 1d , it is is preferably benzoyl or benzoyl substituted by C 1 -C 6 -alkyl or C 2 -C 6 -alkenyl, especially C 1 -C 4 -alkyl or C 2 -C 4 -alkenyl.
  • R 1 in formula I is C 3 -C 12 -alkyl such as propyl or butyl; C 1 -C 4 -alkoxycarbonyl-C 1 -C 2 -alkyl such as methoxycarbonylmethyl, ethoxycarbonylmethyl or propoxycarbonylmethyl; C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxycarbonyl-C 1 -C 2 -alkyl such as ethoxyethoxycarbonylmethyl, ethoxyethoxycarbonylethyl, propoxypropoxycarbonylethyl, propoxypropoxycarbonylmethyl or 3-methoxybutoxycarbonylmethyl; C 2 -C 4 -alkenyl such as vinyl or allyl; benzyl; benzyl in which the phenyl moiety is substituted by one, two or three radicals selected independently of one another from C 1 -C 4 -alkyl, C 2
  • R 1 is C 3 -C 12 -alkyl which is interrupted by one, two or three S heteroatoms and is substituted by SH, such as mercapto-C 3 -C 12 -alkyl or mercapto-C 3 -C 6 -alkyl-S-C 1 -C 2 -alkyl.
  • R 1 is C 1 -C 12 -alkyl, which is substituted by SR 4 , where R 4 is C 2 -C 8 -alkanoyl.
  • R 4 is preferably C 2 -C 4 -alkanoyl.
  • R 1 is C 1 -C 12 -alkyl, which is substituted by OR 5 .
  • R 1 is C 1 -C 12 -alkyl which is substituted by C 1 -C 4 -alkoxycarbonyl.
  • R 1 is benzyl which is substituted by C 1 -C 4 -alkanoyl-S-C 1 -C 2 -alkyl.
  • R 1 is benzyl which is substituted by C 1 -C 4 -alkylthio, or benzyl which is substituted by chlorine.
  • R 1 is phenyl which is substituted by NR 6 R 7 .
  • R 6 is preferably C 2 -C 4 -alkanoyl and R 7 is H.
  • R 1 is 5- or 6-membered saturated heterocyclyl comprising besides carbon atoms one or two identical or different heteroatoms selected from N, NH and N(C 1 -C 8 -alkyl).
  • R 1 Suitable examples for R 1 are phenyl, 4-methylphenyl, 4-ethylphenyl, 4-propylphenyl, 4-nitrophenyl, 4-vinylphenyl, 4-allylphenyl, benzoyl, 4-vinylbenzoyl, (2-butoxyethoxy)-ethoxycarbonyl, methyl, ethyl, propyl, butyl, methoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylmethyl, ethoxycarbonylethyl, 3-methoxybutoxycarbonylmethyl, benzyl, phenethyl, benzylsulfanylethoxyethyl, benzylsulfanylpropoxypropyl, phenethylsulfanylethoxyethyl phenethylsulfanylpropoxypropyl, cyclohexyl, cyclohexylmethyl, 4-vinylcyclo
  • a further preferred embodiment of the invention relates to compositions, compounds, methods and uses, wherein in formula I R 1 and R 14 together with the nitrogen atom to which they are attached form a 5-, 6- or 7-membered saturated or unsaturated heterocycle which may comprise a further heteroatom or heteroatomic group selected from O, S, NH, N(C 1 -C 8 -alkyl) and CO and which may carry 1, 2, 3 or 4 substituents independently of one another selected from halogen, cyano, C 1 -C 4 -alkyl, nitro, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy.
  • R 1 and R 14 together with the nitrogen atom to which they are attached form a 5-, 6- or 7-membered saturated heterocycle which may comprise a further heteroatom or heteroatomic group selected from O, S, NH, N(C 1 -C 8 -alkyl).
  • R 1 and R 14 together with the nitrogen atom to which they are attached form a 5-, 6- or 7-membered saturated heterocycle which may comprise a further heteroatom or heteroatomic group selected from O, S, NH, N(C 1 -C 8 -alkyl).
  • Examples are piperidin-1-yl, morpholin-4-yl, thiomorpholin-4-yl or piperazin-1-yl or 4-(C 1 -C 4 -alkyl)piperazin-1-yl.
  • a further preferred embodiment of the invention relates to compositions, compounds, methods and uses, where in formula I R 1 and R 14 together are a divalent bridging group selected from C 2 -C 8 -alkylene which may be interrupted by one or more, e.g. 1, 2 or 3, identical or different groups selected from O, S, N(C 1 -C 8 -alkyl) and CO.
  • a further preferred embodiment of the invention relates to compositions, compounds, methods and uses, wherein in compounds of the formula I comprising at least two radicals R 1 , two radicals R 1 together may be a divalent bridging group having 1 to 20 atoms between the flanking bonds.
  • the bridging group is preferably selected from C 1 -C 10 -alkylene, C 2 -C 10 -alkenylene, phenylene, phenylene-C 1 -C 4 -alkylene, C 1 -C 4 -alkylene-phenylen-C 1 -C 4 -alkylene, heteroarylene, heteroarylene-C 1 -C 4 -alkylene and C 1 -C 4 -alkylene-heteroarylene-C 1 -C 2 -alkylene or.
  • Each alkylene and alkenylene may be interrupted by one or more, e.g.
  • each phenylene and heteroarylene may be substituted by one or more, e.g. 1, or 2 identical or different radicals C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 , and each phenylene and heteroarylene may be substituted by one or more, e.g. 1, or 2 identical or different radicals C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 .
  • a further preferred embodiment of the invention relates to compositions, compounds, methods and uses, wherein R 2 in formula I is COR 8 ; COOR 9 ; CONR 10 R 11 ; C 1 -C 12 -alkyl, C 2- C 12 -alkenyl, where the 2 last-mentioned radicals may be substituted by one or more, e.g. 1, 2, or 3 identical or different radicals R 2a ; C 3 -C 12 -cycloalkyl, which may be substituted by one or more, e.g. 1, 2 or 3, identical or different radicals R 2b ; C 6 -C 10 -aryl, which may be substituted by one or more, e.g.
  • R 2c 1, 2, 3, 4 or 5, identical or different radicals R 2c ; 5- or 6-membered heteroaryl comprising besides carbon atoms one or two heteroatoms selected from N, O and S and which may be substituted by one or more, e.g. 1, 2, 3, 4 or 5, identical or different radicals R 2c ; or pyridinium of the formula where # is the point of attachment to the remainder of the molecule and R 2f is C 1 -C 12 -alkylene-COO-, C 1 -C 12 -alkylene-S(O) 2 O - or C 1 -C 12 -alkylene-OS(O) 2 O - ; where R 2a , R 2b , R 2c , R 8 , R 9 , R 10 and R 11 are as defined and preferably have one of the preferred meanings.
  • R 2a has preferably one of the preferred meanings indicated for R 1a .
  • R 2b has preferably one of the preferred meanings indicated for R 1a .
  • R 2c is preferably C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl or nitro.
  • R 2 is C 1 -C 6 -alkyl; C 5 -C 8 -cycloalkyl; C 1 -C 4 -alkoxycarbonyl; CO(N-(C 1 -C 8 -alkyl) 2 ); -C(O)O(CH 2 CH 2 O) x (C 1 -C 4 -aikyl) with x being 1, 2, 3, 4, 5 or 6; -C(O)O-C 1 -C 4 -alkyl-phenyl; pyridyl; phenyl; phenyl which is substituted by one or two radicals selected from nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, and C 1 -C 4 -alcoxycarbonyl; benzyl; benzyl where the phenyl moiety is substituted by one or more, e.g.
  • R 2 is morpholinoamide or C 1 -C 4 -haloalkoxycarbonyl, in particular C 1 -C 4 -fluoroalkoxycarbonyl.
  • R 2 Suitable examples for R 2 are methyl, ethyl, propyl or butyl, cyclopentyl, cyclohexyl, n-propoxycarbonyl, ethoxycarbonyl, methoxycarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, -C(O)O(CH 2 CH 2 O)CH 2 CH 3 , -C(O)O(CH 2 CH 2 O) 2 CH 2 CH 3 , -C(O)O(CH 2 CH 2 O) 3 CH 2 CH 3 , -C(O)O(CH 2 CH 2 O) 4 CH 2 CH 3 , benzyloxycarbonyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl; 4-nitrophenyl, 4-methoxycarbonylphenyl, 4-ethoxycarbonylphenyl, 4-propoxycarbonylphenyl or Further suitable examples for R 2 are morpholinoamide and
  • a further preferred embodiment of the invention relates to compositions, compounds, methods and uses, wherein in formula I -X-R 1 together with R 2 are X-(O-C 1 -C 20 -alkylene)-Y, X-(S-C 1 -C 20 -alkylene)-Y or X-(N(R 6 )-C 1 -C 20 -alkylene)-Y.
  • Y is a direct bond and R 6 is as defined above, preferably C 1 -C 8 -alkyl.
  • Suitable examples for this embodiment are compounds where-X-R 1 together with R 2 are -N(C 1 -C 8 -alkyl)-(O-C 2 -C 8 -alkylene)-, -S-(S-C 2 -C 8 -alkylene)- or -N(C 1 -C 8 -alkyl)-(N(C 1 -C 8 -alkyl)-C 2 -C 8 -alkylene)-.
  • -X-R 1 together with R 2 are selected from: where * denotes the point of attachment to the oxime nitrogen atom.
  • -X-R 1 together with R 2 are -X-(C 1 -C 8 -alkylene)-O-C(O)-; -X-(C 3 -C 6 -cycloalkylene)-O-C(O)-; -X-(o-phenylene)-O-C(O)-; X-(C 1 -C 8 -alkylene)-NR 10 -C(O)-; or -X-(C 3 -C 6 -cycloalkylene)-NR 10 -C(O)-; where each alkylene moiety may be substituted by one or more identical or different radicals R 2g , cycloalkylene may be substituted by one or more identical or different radicals R 2h , and o-phenylene may be substituted by one or more identical or different radicals R 2h , where R 10 , R 2g , R 2h and X have one of the meanings given above.
  • X-R 1 together with R 2 and the oxime carbon atom, to which X and R 2 are bound, preferably form a 5- or 6-memberd heterocycle.
  • X is preferably S, -N(benzyl) or N(C 1 -C 8 -alkyl), in particular S, -N(benzyl) or N(C 1 -C 4 -alkyl).
  • -X-R 1 together with R 2 are X-(C 1 -C 8 -alkylene)-S-C(O)-, in particular -S-(C 1 -C 8 -alkylene)-S-C(O)-.
  • X-R 1 and R 2 together with the oxime carbon atom to which they are attached are preferably one of the following rings, with particular preference given to R-1, R-3, R-5, and R-13 where
  • compositions, compounds, methods and uses where in formula I -X-R 1 together with R 2 are -S-C(S)-NR 12- C(O)-, where R 12 is as defined above.
  • X-R 1 and R 2 together with the carbon atom of the oxime group ring to which they are attached form the following ring R-20 where
  • X-R 1 and R 2 together with the carbon atom of the oxime group ring to which they are attached form the following ring R-21 where
  • two radicals R 2 together may be a divalent bridging group having 1 to 20 atoms between the flanking bonds.
  • the bridging group is preferably selected from C 1 -C 10 -alkylene, C 2 -C 10 -alkenylene, phenylene, phenylene-C 1 -C 4 -alkylene, C 1 -C 4 -alkylene-phenylen-C 1 -C 4 -alkylene, heteroarylene, heteroarylene-C 1 -C 4 -alkylene and C 1 -C 4 -alkylene-heteroarylene-C 1 -C 2 -alkylene or.
  • Each alkylene and alkenylene may be interrupted by one or more, e.g.
  • a specific embodiment of the invention relates to compositions, compounds, uses and methods, wherein R 3 in formula I is C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl and C 2 -C 20 -alkynyl may be interrupted by one or more identical or different groups selected from -O-, -S-, -N(R 6 )- and CO, and/or may carry one or more identical or different radicals R 3a , where R 3a is is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 3 -C 20 -cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, heteroaryl and C 6 -C 10 -aryl where the four last-mentioned radicals may carry one or more identical or different radicals R 3aa .
  • R 3aa is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 .
  • R 3 is selected from C 2 -C 12 -alkyl; C 2 -C 12 -alkenyl; phenyl-C 1 -C 4 -alkyl; C 1 -C 6 -haloalkyl, in particular C 1 -C 4 -haloalkyl, especially C 1 -C 4 -fluoroalkyl; C 3 -C 12 -cycloalkyl-C 1 -C 12 -alkyl; C 3 -C 12 -cycloalkyl; heterocyclyl; C 6 -C 10 -aryl; C 3 -C 12 -cycloalkyl which is interrupted by one or two CO and/or may be substituted by one or more, e.g.
  • heterocyclyl which is interrupted by one or two CO and/or may be substituted by one or more, e.g. 1, 2, 3, 4, 5 or 6 C 1 -C 12 -alkyl; C 3 -C 12 -cycloalkyl-C 1 -C 12 -alkyl where the cycloalkyl moiety is interrupted by one or two CO and/or may be substituted by one or more, e.g. 1, 2, 3, 4, 5 or 6 C 1 -C 12 -alkyl; and C 6 -C 10 -aryl which may be substituted by one or more, e.g.
  • R 3 is C 2 -C 12 -alkyl which is substituted by C 1 -C 4 -alkoxycarbonyl. In a further embodiment R 3 is naphthyl-C 1 -C 4 -alkyl.
  • R 3 is heteroaryl, in particular 5- or 6-membered heteroaryl comprising besides carbon ring members 1 or 2 heteroatoms selected from O, S and N.
  • R 3 is phenyl-C 1 -C 4 -alkyl, where the phenyl moiety is substituted by one or more radicals selected from F, Cl, Br, I, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -alkoxycarbonylsulfanyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkyl, phenyl, phenoxy and cyano.
  • R 3 is C 2 -C 6 -alkyl, in particular ethyl, propyl or butyl; C 3 -C 12 -cycloalkyl in particular cyclopentyl or cyclohexyl; C 3 -C 12 -cycloalkyl-C 1 -C 6 -alkyl where the cycloalkyl moiety is interrupted by one or two carbonyl groups and carries 1, 2, 3 or 4 C 1 -C 4 -alkyl, in particular camphoryl, especially camphor-10-yl; C 2 -C 6 -alkenyl such as vinyl or allyl; phenyl; naphthyl; phenyl which carries one, two, three, four or five substituents selected independently of one another from nitro, fluorine, C 1 -C 4 -alkyl, C 1 -C 4 -fluoroalkyl, C 1 -C 4 -alkoxycarbonyl
  • R 3 is 5- or 6-membered saturated heterocyclyl comprising besides carbon atoms 1 or 2 heteroatoms or heteroatomic groups selected from O, S, SO, SO 2 , NH and N(C 1 -C 8 -alkyl).
  • R 3 is thienyl.
  • R 3 is phenyl-C 1 -C 2 -alkyl.
  • R 3 is phenyl-C 1 -C 2 -alkyl, where the phenyl moiety is substituted by one or more radicals selected from Cl, C 1 -C 4 -alkoxycarbonylsulfanyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, phenoxy, phenyl and cyano.
  • R 3 is C 2 -C 4 -alkyl; C 1 -C 4 -fluroalkyl; camphor-10-yl; C 2 -C 4 -alkenyl; benzyl; benzyl which is substituted by one or two substituents selected from C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and nitro; naphthyl; phenyl; or phenyl which is substituted by one, two, three, four or five substituents selected from nitro, fluorine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl and C 2 -C 4 -alkenyl.
  • R 3 is phenyl which carries one, two, three, four or five substituents selected independently of one another from chlorine, cyano, NHC(O)-C 1 -C 4 -alkyl, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxy, C 1 -C 4 -fluoroalkyl, C 1 -C 4 -alkoxycarbonyl and C 2 -C 4 -alkenyl.
  • R 3 is thienyl or 5- or 6-membered saturated heterocyclyl comprising besides carbon atoms 1 or 2 heteroatoms or heteroatomic groups selected from O and S.
  • R 3 Suitable examples for R 3 are methyl, ethyl, propyl, vinyl, allyl, trifluoromethyl, camphor-10-yl, 2-naphthyl, 1-naphthyl, phenyl, pentafluorophenyl, 4-methylphenyl, 4-ethylphenyl, 4-methoxyphenyl, 4-ethoxyphenyl, 4-nitrophenyl, 4-vinylphenyl, 4-trifluoromethylphenyl, 3-nitrophenyl, 3-methylphenyl, 3-ethylphenyl, 3-vinylphenyl, 3,5-diethoxycarbonylphenyl, benzyl, 4-methylbenzyl, 4-ethylbenzyl, 4-nitrobenzyl, 4-vinylbenzyl, 3-nitrobenzyl, 3-methylbenzyl, 3-ethylbenzyl or 3-vinylbenzyl.
  • Further examples are 4-methylsulfanylphenyl, 4-acetylaminophenyl, 4-methoxyphenyl, 4-acetylsulfanylmethylbenzyl, 4-cyanobenzyl, 4-chlorobenzyl, 4-methoxycarbonylbenzyl, 4-chlorobenzyl, 1-naphthylmethyl, 2-naphthylmethyl, 4-phenoxybenzyl, 4-vinylbenzyl, 3,4-dimethylsulfanylbenzyl, 3,5-ditrifluoromethylbenzyl, 4-tert-butylbenzyl, 4-phenylbenzyl, 2-thienyl, 3-thienyl, tetrahydropyran-3-yl and tetrahydrofuran-2-ylmethyl.
  • compositions, compounds, methods and uses where in formula I -X-R 1 together with R 3 are a divalent radical selected from X-(C 1 -C 10 -alkylene)-Z, X-(C 2 -C 10 -alkenylene)-Z, X-(C 3 -C 20 -cycloalkylene)-Z, X-(heterocycloalkylene)-Z, X-(o-phenylene)-Z, where X is as defined above and Z is attached to the sulfur atom of the sulfonate group and has one of the meanings given above, preferably a single bond.
  • the following structural units are obtained
  • Another preferred embodiment of the invention relates to compositions, compounds, methods and uses, where in formula I a is 1 and b and c are both 0.
  • Q is R 1 and has preferably one the meanings mentioned as being preferred for R 1 .
  • Q is a divalent radical.
  • Q is Q is L-C 1 -C 30 -alkylene-L, L-C 3 -C 16 -cycloalkylene-L, L-heterocycloalkylene-L, L-C 6 -C 20 -arylene-L, L-C 1 -C 30 -alkylene-L 2 -L, L-C 3 -C 16 -cycloalkylene-L 1 -C 3 -C 16 -cycloalkylene-L or L-C 6 -C 20 -arylene-L 1 -C 6 -C 20 -arylene-L, where each alkylene may be interrupted by one or more identical or different non-adjacent O or S, where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO, and
  • Q is L-C 1 -C 30 -alkylene-L, L-C 3 -C 16 -cycloalkylene-L, L-heterocycloalkylene-L, L-C 6 -C 20 -arylene-L, L-C 1 -C 30 -alkylene-L 2 -L, L-C 3 -C 16 -cycloalkylene-L 1 -C 3 -C 16 -cycloalkylene-L or L-C 6 -C 20 -arylene-L 1 -C 6 -C 20 -arylene-L, where each alkylene may be interrupted by one or more identical or different non-adjacent phenylene, OC(O), C(O)O, O or S, where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO, and where L is a single bond, C(S)O or C(S)NR 12 , more preferably a
  • Q is C 1 -C 30 -alkylene; C 1 -C 30 -alkylene which is interrupted once, twice, three times, four times, five times or six times by non-adjacent O; C 1 -C 30 -alkylene which is interrupted once, twice, three times, four times, five times or six times by non-adjacent S; phenylen; naphthylen; phenylen-O-phenylen; phenylen-S-phenylen; napthylen-O-naphthylen; or napthylen-S-naphthylen.
  • Q is phenylen-S-phenylen; C 1 -C 10 -alkylene; or C 1 -C 20 -alkylene which is interrupted by one, two, three or four more non-adjacent atoms selected from O and S.
  • examples of Q are linear C 1 -C 10 -alkylene, branched C 1 -C 10 -alkylene, -CH 2 -CH 2 -O-CH 2 -CH 2 -, -CH 2 -CH 2 -S-CH 2 -CH 2 -, -CH 2 -CH 2 -O-CH 2 -CH 2 -O-CH 2 -CH 2 -, -CH 2 -CH 2 -S-CH 2 -CH 2 -S-CH 2 -CH 2 -, where * denotes the point of attachment to X.
  • Q is C 1 -C 10 -alkylene which is interrupted by 1, 2, 3 or 4 groups selected from O, S, C(O)O and OC(O); examples are -CH 2 -C(O)-O-CH 2 -CH 2 -CH 2 -CH 2 -O-C(O)-CH 2 -, 1,4-phenylene, CH 2 C(O)-O-CH 2 -CH 2 -O-C(O)-CH 2 .
  • Q is a divalent radical.
  • Q is L 5 -C 1 -C 30 -alkylene-L 5 , L 5 -C 3 -C 16 -cycloalkylene-L 5 , L 5 -heterocycloalkylene-L 5 , L 5 -C 6 -C 20 -arylene-L 5 , L 5 -C 3 -C 16 -cycloalkylene-L 7 -C 3 -C 16 -cycloalkylene-L 5 or L 5 -C 6 -C 20 -arylene-L 7 -C 6 -C 20 -arylene-L 5 , where alkylene may be interrupted by one or more identical or different non-adjacent O or S, where each cycloalkylene and each heterocycloalkylene may be interrupted by one or
  • L 5 is a single bond, S, O, C(O), OC(O) or C(O)O.
  • Q is C 1 -C 30 -alkylene; -C(O)O-C 1 -C 30 -alkylene-O-C(O)-; C 1 -C 30 -alkylene which is interrupted once, twice, three times, four times, five times or six times by non-adjacent O; C 1 -C 30 -alkylene which is interrupted once, twice, three times, four times, five times or six times by non-adjacent S; -C(O)O-C 1 -C 30 -alkylene-O-C(O)- in which alkylene is interrupted once, twice, three times, four times, five times or six times by non-adjacent O; phenylen; naphthylen; phenylen-O-phenylen; phenylen-S-
  • Q is C 1 -C 10 -alkylene which may be interrupted by one, two, three or four more non-adjacent atoms selected from O and S.
  • examples of Q are linear or branced C 1 -C 10 -alkylene, -CH 2 -CH 2 -O-CH 2 -CH 2 -, -CH 2 -CH 2 -S-CH 2 -CH 2 -, -CH 2 -CH 2 -O-CH 2 -CH 2 -O-CH 2 -CH 2 -, -CH 2 -CH 2 -S-CH 2 -CH 2 -CH 2 - or -C(O)O-C 2 -C 4 -alkylene-O-C(O)-.
  • Q is -C(O)O-C 1 -C 30 -alkylene-O-C(O)-.
  • compositions, compounds, methods and uses where in formula I b is 2 or 3 and -X-R 1 together with a carbon atom or nitrogen atom of Q form a 5-, 6- or 7- membered ring via X-(C 1 -C 6 -alkylene)-N(R 10 )CO, X-(C 3 -C 6 -cycloalkylene)-N(R 10 )CO, X-(o-phenylene)-N(R 10 )CO, or S-C(S)-N(R 12 )-CO, where R 10 and R 12 are as defined above and preferably have one of the preferred meanings.
  • Q is a divalent radical.
  • Q is selected from C 1 -C 30 -alkylene, C 3 -C 16 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene, C 3 -C 16 -cycloalkylene-L 11 -C 3 -C 16 -cycloalkylene, C 6 -C 20 -arylene-L 11 -C 6 -C 20 -arylene, where alkylene may be interrupted by one or more identical or different non-adjacent O or S, where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO, and where L 11 is a single bond, O or S.
  • Q is C 1 -C 30 -alkylene; C 1 -C 30 -alkylene which is interrupted once, twice, three times, four times, five times or six times by non-adjacent O; C 1 -C 30 -alkylene which is interrupted once, twice, three times, four times, five times or six times by non-adjacent S; phenylen; naphthylen; phenylen-O-phenylen; phenylen-S-phenylen; napthylen-O-naphthylen; or napthylen-S-naphthylen.
  • Q is phenylen or naphthylene.
  • examples of Q are 1,3-phenylen, 1,4-phenylen, 1,8-naphthylen and 2,7-naphthylen.
  • Q is a divalent radical.
  • Q is selected from C 1 -C 30 -alkylene, C 3 -C 16 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene, C 3 -C 16 -cycloalkylene-L 11 -C 3 -C 16 -cycloalkylene, C 6 -C 20 -arylene-L 11 -C 6 -C 20 -arylene, where alkylene may be interrupted by one or more identical or different non-adjacent O or S, where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO, and where L 11 is a single bond, O or S.
  • Q is C 1 -C 30 -alkylene; C 1 -C 30 -alkylene which is interrupted once, twice, three times, four times, five times or six times by non-adjacent O; C 1 -C 30 -alkylene which is interrupted once, twice, three times, four times, five times or six times by non-adjacent S; phenylen; naphthylen; phenylen-O-phenylen; phenylen-S-phenylen; napthylen-O-naphthylen; or napthylen-S-naphthylen.
  • Q is CH 2 -phenylene-CH 2 , phenylen2 or naphthylene.
  • examples of Q are CH 2 -(1,4-phenylene)-CH 2 -, 1,3-phenylen, 1,4-phenylen, 1,8-naphthylen and 2,7-naphthylen.
  • Q is a trivalent linker.
  • Q is selected from C 1 -C 30 -alkanetriyl, C 3 -C 16 -cycloalkanetriyl, C 6 -C 20 -arenetriyl, C 1 -C 30 -alkanetriyl-L 14 -L 15 , C 1 -C 30 -alkylene-L 14 -L 16 , C 6 -C 20 -arenetriyl-L 14 -L 15 -C 6 -C 20 -arylene, and C 6 -C 20 -arylene-L 14 -L 15 -C 3 -C 16 -cycloalkanetriyl where each alkanetriyl and each alkylene may be interrupted by one or more, e.g.
  • each cycloalkanetriyl may be interrupted by one or more CO groups, where L 14 is a single bond, O or S, L 15 is C 3 -C 20 -cycloalkylene, heterocycloalkylene or C 6 -C 20 -arylene and where L 16 is arenetriyl.
  • Q is C 1 -C 30 -alkanetriyl or C 1 -C 30 -alkanetriyl which is interrupted by one, two, three, four, five, or six non-adjacent groups independently of one another selected from O, S, NR 6 , NR 10 C(O), CONR 10 , CO, OC(O) and C(O)O, where R 6 and R 10 are as defined above and preferably have one of the preferred meanings.
  • examples of Q are where
  • Another preferred embodiment of the invention relates to compositions, compounds, methods and uses, where in formula I the sum of a + b + c is 4.
  • Q is a tetravaalent linker. Suitable examples are C 1 -C 30 -alkanetetrayl which may be interrupted by one or more, preferably 1, 2, 3, 4, 5, 6, 7, 8 or more than 8 groups L 18 . L 18 is preferably O, S, NR 6 , CO, C(O)O, OC(O), C(O)NR 10 or NR 10 C(O).
  • examples of Q are Another preferred embodiment of the invention relates to compositions, compounds, methods and uses, where in formula I the sum of a + b + c is 6.
  • Q is a hexavalent linker.
  • Sutiable examples are C 2 -C 30 -alkanehexayl which may be interrupted by one or more, preferably 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or more than 12 groups L 19 .
  • L 19 is preferably O, S, NR 6 , CO, C(O)O, OC(O), C(O)NR 10 or NR 10 C(O).
  • variables R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 independently of each other, preferably have one of the following meanings:
  • Q is a divalent linker, which is selected from C 1 -C 30 -alkylene, C 3 -C 16 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene, C 3 -C 16 -Cycloalkylene-L 11 -C 3 -C 16 -Cycloalkylene, C 6 -C 20 -arylene-L 11 -C 6 -C 20 -arylene, where alkylene may be interrupted by one or more identical or different non-adjacent phenylene, C(O)O, OC(O); O or S, where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO, and where L 11 is a single bond, O or S.
  • compositions, compounds, methods and uses where in formula I X is S, and R 1 and R 2 in combination have the following meanings:
  • compositions, compounds, methods and uses where in formula I X-R 1 and R 2 together with the oxime carbon atom to which they are attached are a ring R-1, R-3, R-5, R-13 or R-19 where * denotes the point of attachment to the oxime nitrogen atom.
  • -X-R 1 together with R 2 are -S-(C 1 -C 8 -alkylene)-S-C(O)-.
  • -X-R 1 together with R 2 are -S-C(S)-NR 12 -C(O)-, where R 12 is as defined above.
  • X-R 1 and R 2 together with the carbon atom of the oxime group ring to which they are attached form the ring R-21 where
  • R 3 is preferably selected from C 2 -C 12 -alkyl, C 2 -C 12 -alkenyl, phenyl-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 12 -cycloalkyl, C 3 -C 12 -cycloalkyl-C 1 -C 12 -alkyl, heterocyclyl and C 6 -C 10 -aryl, where each cycloalkyl and heterocyclyl may be interrupted by one or two CO and/or may be substituted by one or more C 1 -C 12 -alkyl and where aryl may be substituted by one or more identical or different radicals selected from C 1 -C 12 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, CN,
  • compositions, compounds, methods and uses where in formula I a is 2, b and c are both 0.
  • X is S
  • R 2 is C 1 -C 12 -alkyl
  • Q is C 1 -C 30 -alkylene which may be interrupted by one, two, three or four non-adjacent heteroatoms selected from O and S.
  • X is S
  • R 2 is COOR 9
  • Q is C 6 -C 20 -arylen-S-C 6 -C 20 -arylen.
  • R 9 is as defined above and preferably has one of the preferred meanings.
  • compositions, compounds, methods and uses where in formula I a is 3, b and c are both 0, more preference is likewise given to those compounds, in which X is S, R 2 is COOR 9 and Q is C 1 -C 20 -alkanetriyl which may be interrupted by 3, 4, 5, 6, 7, 8, or 9 identical or different groups selected from O, S, NR 6 , CO, C(O)O.
  • R 9 is as defined above and preferably has one of the preferred meanings.
  • compositions, compounds, methods and uses where in formula I b is 2, a and c are both 0, more preference is likewise given to those compounds, in which X is S, R 1 is C 1 -C 12 -alkyl which is substituted by COOR 9 and Q is C 1 -C 30 -alkylene which may be interrupted once, twice, three times, four times, five times or six times by non-adjacent O or S.
  • R 9 is as defined above and preferably has one of the preferred meanings.
  • compositions, compounds, methods and uses where in formula I c is 2, a and b are both 0, more preference is likewise given to those compounds, in which X is S, R 2 is COOR 9 and Q is C 6 -C 20 -arylen.
  • R 3 is is C 2 -C 4 -alkyl, C 2 -C 6 -alkenyl, phenyl or benzyl where each of the two last mentioned radicals may be unsubstituted or may carry one, two, three, four or five radicals independently of one another selected fluorine, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -fluoroalkyl, C 1 -C 4 -alkoxycarbonyl and C 2 -C 6 -alkenyl; and -X-R 1 together with R 2 are -X-(C 1 -C 8 -alkylene)-O-C(O)- or -X-(o-phenylene)-O-C(O)- and X is N(C 1 -C 8 -alkyl), N(benzyl
  • compositions, compounds, methods and uses where in formula IA.
  • each R 2 has the same meaning. According to a further particular preferred aspect of this embodiment, each R 2 has different meanings. According to a further preferred aspect of this embodiment, each R 3 has the same meaning. According to a further preferred aspect of this embodiment, each R 3 has different meanings. According to a further preferred aspect of this embodiment, each R 2 has a different meaning and each R 3 has a different meaning.
  • compositions, compounds, methods and uses where in formula IC.2
  • compositions, compounds, methods and uses where in formula ID where
  • Oxime sulfonates of the formula I can generally be prepared by methods described in the literature or in the experimental part.
  • oxime sulfonates of the formula I can generally be prepared by reacting suitable free oximes with the sulfonic acid halides.
  • oxime sulfonates of the formulae IA, IA.1, IB and IC can be prepared by reacting suitable free oximes of the formula IIA, IIA,1, IIB or IIC with the sulfonic acid halides as shown in Scheme 1.
  • R 1 , R 2 , R 3 and Q are as defined above, a is 2 or 3 b is 2 or 3 and c is 2 or 3, Hal is halogen, preferably chlorine.
  • oxime IIC is identical with the oxime IIA. Furthermore, a skilled person will readily understand that 2 equivalents of compound IIC are required as starting material if c is 2 in the compound IC. 3 equivalents of compound IIC are required as starting material if c is 3 in the compound IC.
  • reaction usually are carried out in pyridine as solvent and base or in an inert solvent such as for example toluene, tetrahydrofuran (THF) or dimethylformamide (DMF) in the presence of a base for example a tertiary amine, such as triethylamine and diisopropylethylamine, or a secondary amine, such as diisopylamine or by reaction of the salt of an oxime with the desired acid chloride.
  • a base for example a tertiary amine, such as triethylamine and diisopropylethylamine, or a secondary amine, such as diisopylamine or by reaction of the salt of an oxime with the desired acid chloride.
  • a base for example a tertiary amine, such as triethylamine and diisopropylethylamine, or a secondary amine, such as diisopylamine or by reaction of the salt
  • the oxime sulfonates of the formulae IA and IA.1 can be also prepared by reacting a suitable sulfonyloxyimidoyl chloride of the formula IIIA with a substance carrying one or more SH or NH groups, sulfinic acids or those salts as shown in Scheme 2.
  • R 2 , R 3 , X and Q are as defined above, a is 1, 2, 3 or 4.
  • the oximes required as the starting materials can be obtained by a variety of methods described in literatures, for example, the reaction of ketones with hydroxylamine or its salt in polar solvents like ethanol or aqueous ethanol.
  • a base such as sodium acetate is added to control the pH of the reaction mixture. It is well known that the rate of the reaction is pH-dependent, and the base can be added at the beginning or continuously during the reaction.
  • Basic solvents such as pyridine can also be used as base and/or solvent or cosolvent.
  • the reaction temperature is generally the refluxing temperature of the mixture, usually about 60-120°C.
  • oximes Another convenient synthesis of oximes is the reaction of a suitable oximidoyl halide, such as oximidoyl chloride or oximidoyl bromide with a thiol as described, for example, in Synlett, 937 (2001 ) or EP64091 and with a primary or secondary amine as described, for example, in J. Chem. Soc., Perkin Trans. 1, 1999, 1789 , J. Heterocyclic Chem., 43, 579 (2006 ). or Tetrahedron Letters, 47(51), 9029 (2006 ).
  • a suitable oximidoyl halide such as oximidoyl chloride or oximidoyl bromide
  • a thiol as described, for example, in Synlett, 937 (2001 ) or EP64091
  • a primary or secondary amine as described, for example, in J. Chem. Soc., Perkin Trans. 1, 1999, 1789 , J. Heterocycl
  • reaction are usually carried out in an inert solvent like toluene, dioxane, tetrahydrofuran (THF), diethyl ether, dichloromethane, dimethylformamide (DMF), methanol or aqueous methanol in the presence of a base, for example, a tertiary amine, such as triethylamine, or metal hydroxide, such as NaOH, LiOH and KOH.
  • a base for example, a tertiary amine, such as triethylamine, or metal hydroxide, such as NaOH, LiOH and KOH.
  • the oximidoyl halides can be obtained by reacting the corresponding aldoximes with halogenation reagents, for example, N-chlorosccinimide (NCS) as described, for example, in J. Chem. Soc., Perkin Trans. 1, 2627 (1991 ) or J. Org. Chem., 45, 3916 (1980 ), N-bromosccinimide (NBS), chlorine as described, for example, in EP64091 or, bromine or tert-butyl hypochlorite.
  • NCS N-chlorosccinimide
  • NSS N-bromosccinimide
  • chlorine as described, for example, in EP64091 or, bromine or tert-butyl hypochlorite.
  • oximidoyl chloride Another synthesis of oximidoyl chloride is the oximination of glycine ethyl ester hydrochloride with sodium nitrite in aq. HCl solution as described, for example, in J. Org. Chem., 48(3), 366 (1983 ).
  • the described syntheses can result in the formation of isomeric forms of the compounds of formulae I, IA.1, IA, IB, IC or ID.
  • the double bond of the oximino group can exist in both the syn (cis, Z) and the anti (trans, E) form or as mixtures of the two geometrical isomers.
  • both the individual geometrical isomers and any mixtures of two geometrical isomers can be used.
  • the invention accordingly also relates to mixtures of isomeric forms of the compounds of formulae I, IA.1, IA, IB and IC.
  • the compounds of formulae I, IA.1, IA, IB and IC can be used as thermal curing promoters to enhance the polymerization, especially in the post-baking process when manufacturing liquid crystal display components such as color filters, photospacer, overcoat and interlayer dielectric.
  • the compounds of formulae I, IA.1, IA, IB, IC and ID can be used in principle to polymerize all types of ethylenically unsaturated compounds.
  • Suitable ethylenically unsaturated compounds (b) are monomers or oligomers that can be polymerized in a manner known per se using the methods of free-radical polymerization.
  • (meth)acrylate in the context of the present application is meant to refer to the acrylate as well as to the corresponding methacrylate.
  • compound (b) is selected from esters of ⁇ , ⁇ -ethylenically unsaturated monocarboxylic and dicarboxylic acids with C 1 -C 20 alkanols, vinylaromatics, esters of vinyl alcohol with C 1 -C 30 monocarboxylic acids, ethylenically unsaturated nitriles, vinyl halides, vinylidene halides, monoethylenically unsaturated carboxylic and sulfonic acids, esters of ⁇ , ⁇ -ethylenically unsaturated monocarboxylic and dicarboxylic acids with C 2 -C 30 alkanediols, amides of ⁇ , ⁇ -ethylenically unsaturated monocarboxylic and dicarboxylic acids with C 2 -C 30 amino alcohols which contain a primary or secondary amino group, primary amides of ⁇ , ⁇ -ethylenically unsaturated monocarboxylic acids and their N-alkyl
  • Suitable ethylenically unsaturated carboxylic acids and sulfonic acids or their derivatives are acrylic acid, methacrylic acid, ethacrylic acid, ⁇ -chloroacrylic acid, crotonic acid, maleic acid, maleic anhydride, itaconic acid, citraconic acid, mesaconic acid, glutaconic acid, aconitic acid, fumaric acid, the monoesters of monoethylenically unsaturated dicarboxylic acids having 4 to 10, preferably 4 to 6, C atoms, e.g., monomethyl maleate, vinylsulfonic acid, allylsulfonic acid, sulfoethyl acrylate, sulfoethyl methacrylate, sulfopropyl acrylate, sulfopropyl methacrylate, 2-hydroxy-3-acryloyloxypropylsulfonic acid, 2-hydroxy-3-methacryloyloxypropylsul
  • Suitable derivatives of ethylenically unsaturated carboxylic acids and sulfonic acids are their salts.
  • Suitable salts of acrylic acid or methacrylic acid are, for example, (C 1 -C 4 -alkyl) 4 ammonium or (C 1 -C 4 -alkyl) 3 NH salts, e. g.
  • the tetramethylammonium, tetraethylammonium, trimethylammonium or triethylammonium salts the trimethyl-2-hydroxyethylammonium or triethyl-2-hydroxyethylammonium salts, the dimethyl-2-hydroxyethylammonium or diethyl-2-hydroxyethylammonium salts.
  • Suitable esters of ⁇ , ⁇ -ethylenically unsaturated monocarboxylic and dicarboxylic acids with C 1 -C 20 alkanols are methyl (meth)acrylate, methyl ethacrylate, ethyl (meth)acrylate, ethyl ethacrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, tert-butyl ethacrylate, n-hexyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, 1,1,3,3-tetramethylbutyl (meth)acrylate, ethylhexyl (meth)acrylate, n-nonyl (meth)acrylate,
  • Preferred vinylaromatics are styrene, 2-methylstyrene, 4-methylstyrene, 2-(n-butyl)styrene, 4-(n-butyl)styrene, 4-(n-decyl)styrene, and, with particular preference, styrene.
  • Suitable esters of vinyl alcohol with C 1 -C 30 monocarboxylic acids are, for example, vinyl formate, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl laurate, vinyl stearate, vinyl propionate, versatic acid vinyl esters, and mixtures thereof.
  • Suitable ethylenically unsaturated nitriles are acrylonitrile, methacrylonitrile, and mixtures thereof.
  • Suitable vinyl halides and vinylidene halides are vinyl chloride, vinylidene chloride, vinyl fluoride, vinylidene fluoride, and mixtures thereof.
  • Suitable esters of ⁇ , ⁇ -ethylenically unsaturated monocarboxylic and dicarboxylic acids with C 2 -C 30 alkanediols are, for example, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxyethyl ethacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 3-hydroxybutyl acrylate, 3-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, 6-hydroxyhexyl acrylate, 6-hydroxyhexyl methacrylate, 3-hydroxy-2-ethylhexyl acrylate, 3-hydroxy-2-ethylhexyl methacrylate, etc.
  • Suitable primary amides of ⁇ , ⁇ -ethylenically unsaturated monocarboxylic acids and their N alkyl and N,N-dialkyl derivatives are acrylamide, methacrylamide, N-methyl(meth)acrylamide, N-ethyl(meth)acrylamide, N-propyl(meth)acrylamide, N-(n-butyl)(meth)acrylamide, N-(tert-butyl)(meth)acrylamide, N-(n-octyl)(meth)acrylamide, N-(1,1,3,3-tetramethylbutyl)(meth)acrylamide, N-ethylhexyl(meth)acrylamide, N-(n-nonyl)(meth)acrylamide, N-(n-decyl)(meth)acrylamide, N-(n-undecyl)(meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(
  • N-vinyllactams and their derivatives are, for example, N-vinylpyrrolidone, N-vinylpiperidone, N-vinylcaprolactam, etc.
  • Suitable open-chain N-vinylamide compounds are, for example, N-vinylformamide, N-vinyl-N-methylformamide, N-vinylacetamide, N-vinylpropionamide, N-vinylbutyramide, etc.
  • Suitable esters of ⁇ , ⁇ -ethylenically unsaturated monocarboxylic and dicarboxylic acids with amino alcohols are N,N-dimethylaminomethyl (meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethylacrylate, N,N-dimethylaminopropyl (meth)acrylate, N,N-diethylaminopropyl (meth)acrylate and N,N-dimethylaminocyclohexyl (meth)acrylate.
  • Suitable amides of ⁇ , ⁇ -ethylenically unsaturated monocarboxylic and dicarboxylic acids with diamines which contain at least one primary or secondary amino group are N-[2-(dimethylamino)ethyl]acrylamide, N-[2-(dimethylamino)ethyl]methacrylamide, N-[3-(dimethylamino)propyl]acrylamide, N-[3-(dimethylamino)propyl]methacrylamide, N-[4-(dimethylamino)butyl]acrylamide, N-[4-(dimethylamino)-butyl]methacrylamide, N-[2-(diethylamino)ethyl]acrylamide, N-[4-(dimethylamino)cyclohexyl]acrylamide, N-[4-(dimethylamino)cyclohexyl]methacrylamide, etc.
  • Suitable monomers (b) are, furthermore, N,N-diallylamines and N,N-diallyl-N-alkylamines and their acid addition salts and quaternization products.
  • Alkyl here is preferably C 1 -C 24 alkyl. Preference is given to N,N-diallyl-N-methylamine and to N,N-diallyl-N,N-dimethylammonium compounds, such as the chlorides and bromides, for example.
  • suitable monomers (b) are vinyl- and allyl-substituted nitrogen heterocycles, such as N-vinylimidazole, N-vinyl-2-methylimidazole, and vinyl- and allyl-substituted heteroaromatic compounds, such as 2- and 4-vinylpyridine, 2- and 4-allylpyridine, and the salts thereof.
  • Suitable C 2 -C 8 monoolefins and nonaromatic hydrocarbons having at least two conjugated double bonds are, for example, ethylene, propylene, isobutylene, isoprene, butadiene, etc.
  • silyl group-containing (meth)acrylates are silyloxy-C 2 -C 4 -(meth)alkyl acrylates, e.g. 2-trimethylsilyloxyethyl acrylate or methacrylate (TMS-HEA, TMS-HEMA).
  • Examples of (C 1 -C 4 -alkyl) 3 -silyl-C 2 -C 4 alkyl (meth)acrylates are 2-trimethylsilylethyl acrylate or methacrylate and 3-trimethylsilyl-n-propyl acrylate or methacrylate.
  • compound (b) is selected from acrylic acid, methacrylic acid, maleic anhydride, acrylic acid derivatives, styrene, vinyl acetate, vinyl halides and vinylidene halides, acrolein, vinylpyrrolidone, vinylimidazole, alkenes, conjugated dienes and mixtures thereof.
  • heterocycyl-(C 2 -C 4 -alkyl) (meth)acrylates are 2-(N-morpholinyl, 2-pyridyl, 1-imidazolyl, 2-oxo-1-pyrrolidinyl, 4-methylpiperidin-1-yl or 2-oxoimidazolidin-1-yl) ethyl acrylate or methacrylate.
  • Suitable polyether (meth)acrylates (b) are compounds of the general formula (A) in which the sequence of the alkylene oxide units is arbitrary,
  • k is an integer from 3 to 50, more particularly 4 to 25.
  • I is an integer from 3 to 50, more particularly 4 to 25.
  • R a in the formula (AA) is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, n-pentyl, n-hexyl, octyl, 2-ethylhexyl, decyl, lauryl, palmityl or stearyl.
  • R b is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl or n-hexyl, more particularly hydrogen, methyl or ethyl.
  • R b is hydrogen or methyl.
  • Y in the formula (A) is O.
  • the polymerizable composition according to the invention preferably comprises the component (b) in an amount of from 0.01 to 50% by weight, more preferably 0.1 to 40% by weight, in particular 0.5 to 30% by weight, based on the total weight of the composition.
  • composition according to the invention preferably comprises at least one photoinitiator (c) as further component.
  • composition according to the invention preferably comprises at least one binder polymer (d) as further component.
  • composition according to the invention preferably comprises at least one further component (e) selected from
  • composition according to the invention preferably comprises at least one additive (f) selected from solvents, reinforcing materials, flow control assistants, UV stabilizers, heat stabilizers, weatherability improvers, rheology modifiers, flame retardants, antioxidants, discoloration inhibitors, biocides, antistatic agents, plasticizers, lubricants, slip additives, wetting agents, film-forming assistants, adhesion promoters, corrosion inhibitors, antifreeze agents, defoamers, mold release agents, etc., and mixtures thereof.
  • additive selected from solvents, reinforcing materials, flow control assistants, UV stabilizers, heat stabilizers, weatherability improvers, rheology modifiers, flame retardants, antioxidants, discoloration inhibitors, biocides, antistatic agents, plasticizers, lubricants, slip additives, wetting agents, film-forming assistants, adhesion promoters, corrosion inhibitors, antifreeze agents, defoamers, mold release agents, etc., and mixtures thereof.
  • Suitable photoinitiators (c) are described in the following with regard to a polymerizable composition comprising an alkaline developable resin (d). This disclosure is incorporated here for all polymerizable compositions of the invention.
  • Photoinitiators (c) are preferably used in an amount of from 0.001% to 15% by weight, more preferably from 0.01 to 10% by weight, based on the total weight of the polymerizable composition according to the invention.
  • Suitable binder polymers (d) are e.g. physically drying polymer compositions, self-crosslinking polymer compositions, UV-curable polymer compositions, thermosetting polymer compositions, polymer compositions crosslinkable by addition of a crosslinker (2-component dispersions), or dual-cure systems.
  • Suitable thermosetting polymer compositions are described in the following as component (e6).
  • the binder polymer component (d) comprises at least one alkaline developable resin. Suitable alkaline developable resins (d) are described in detail in the following.
  • Binder polymers (d) are preferably used in an amount of from 0.5% to 98% by weight, more preferably from 1 to 95% by weight, in particular from 2 to 90% by weight, based on the total weight of the polymerizable composition according to the invention.
  • Suitable colorants i.e. pigments (e1) and dyes (e2) are described in the following with regard to a polymerizable composition comprising an alkaline developable resin (d). This disclosure is incorporated here for all polymerizable compositions of the invention.
  • Suitable fillers are organic and inorganic fillers, examples being aluminosilicates, such as feldspars, silicates, such as kaolin, talc, mica, magnesite, alkaline earth metal carbonates, such as calcium carbonate, in the form of calcite or chalk, for example, magnesium carbonate, dolomite, alkaline earth metal sulfates, such as calcium sulfate, silicon dioxide, etc.
  • Suitable organic fillers are, for example, textile fibers, cellulose fibers, polyethylene fibers or wood flour. In coating materials, of course, finely divided fillers are preferred. The fillers may be used as individual components.
  • fillers In practice, mixtures of fillers have also proven particularly appropriate, examples being calcium carbonate/kaolin, calcium carbonate/talc. For further details refer to Römpp-Lexikon, Lacke und Druckmaschine, Georg Thieme Verlag, 1998, pages 250 ff ., "fillers”.
  • Fillers (e3) are preferably used in an amount of from 0% to 95% by weight, more preferably from 0.5 to 90% by weight, in particular from 1 to 80% by weight, and especially 4% to 75% by weight, based on the total weight of the polymerizable composition according to the invention.
  • dispersant component e4 as used herein is understood in a broad sense. Dispersant are dispersing agents (including polymeric dispersants), surfactants, texture improving agents, and the like. Suitable dispersants (e4) are described in the following with regard to a polymerizable composition comprising an alkaline developable resin (d). This disclosure is incorporated here for all polymerizable compositions of the invention.
  • the polymerizable compositions of the invention comprise at least one dispersant (e4)
  • it is preferably used in an amount of 0.01% to 50% by weight, preferably 0.1% to 30% by weight, based on the total weight of the polymerizable composition.
  • Suitable (photo)sensitizers (e5) are described in the following with regard to a polymerizable composition comprising an alkaline developable resin (d). This disclosure is incorporated here for all polymerizable compositions of the invention.
  • Sensitizers (e5) are preferably used in an amount of from 0.001% to 15% by weight, more preferably from 0.01 to 10% by weight, based on the total weight of the polymerizable composition according to the invention.
  • Suitable thermosetting compounds (e6) have at least one group selected from an epoxy group, oxetane group and vinyl ether group.
  • Suitable compounds (e6) are:
  • Compounds (e6) which comprise an oxygen- or sulphur-containing saturated heterocycle preferably comprise at least one heterocycle having 3, 4, 5 or 6 ring members.
  • Preferred compounds (e6) which comprise an oxygen- or sulphur-containing saturated heterocycle are selected from compounds containing at least one epoxy group, oxetanes, oxolanes, cyclic acetals, cyclic lactones, thiiranes, thietanes and mixtures thereof.
  • Suitable compounds (e6) containing one epoxy group are ethylene oxide, propylene oxide, styrene oxide, phenyl glycidyl ether, butyl glycidyl ether, etc.
  • compound (e6) is selected from epoxy resins.
  • epoxy resin as utilized in the description of the curable compositions of the present invention, is understood in a broad sense and includes any monomeric, dimeric, oligomeric or polymeric epoxy material containing a plurality (2, 3, 4, 5, 6 or more than 6) of epoxy groups.
  • epoxy resins also encompasses prepolymers which comprise two or more epoxide groups, wherein some of the epoxide groups (oxiran rings) may also have been opened to a hydroxyl group.
  • the term also identifies part-cured epoxy resins, i.e., epoxy resins which have been crosslinked by means of suitable hardeners.
  • component (a) is a part cured epoxy resin, it still contains heat curable epoxy groups that are still capable of undergoing cationic polymerization.
  • epoxy resins also encompasses modified epoxy resins, such as esterified or etherified epoxy resins, obtainable for example by reaction with carboxylic acids or alcohols. Again, modified epoxy resins that are employed in a composition according to the invention still contain heat curable epoxy groups that are still capable of undergoing cationic polymerization.
  • a complete definition of the term “epoxy resins” is found for example in Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, on CD-ROM, 1997, Wiley-VCH, in the "Epoxy Resins" secti on.
  • Epoxy resins derived from epichlorohydrin are referred to as glycidyl-based resins.
  • Novolaks are prepared by the acid-catalyzed condensation of formaldehyde and phenol or cresol. The epoxidation of the novolaks leads to epoxy novolaks.
  • glycidyl-based epoxy resins derive from glycidyl ethers of aliphatic diols, such as butane-1,4-diol, hexane-1,6-diol, pentaerythritol or hydrogenated bisphenol A; aromatic glycidylamines, an example being the triglycidyl adduct of p-aminophenol or the tetraglycidylamine of methylenedianilide; heterocyclic glycidylimides and amides, e.g., triglycidyl isocyanurate; and glycidyl esters, such as the diglycidyl ester of dimeric linoleic acid, for example.
  • glycidyl ethers of aliphatic diols such as butane-1,4-diol, hexane-1,6-diol, pentaerythritol
  • the epoxy resins (e6) may also derive from other epoxides (non-glycidyl ether epoxy resins).
  • epoxides non-glycidyl ether epoxy resins
  • diepoxides of cycloaliphatic dienes such as 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate and 4-epoxyethyl-1,2-epoxycyclohexane.
  • Suitable oxetanes (e6) are trimethylene oxide, 3,3-dimethyloxetane, 3,3-di(chloromethyl) oxetane, etc.
  • Suitable oxolanes are tetrahydrofuran, 2,3-dimethyltetrahydrofuran, etc.
  • Suitable cyclic acetals (e6) are trioxan, 1,3-dioxolane, 1,3, 6-trioxacyclooctane, etc.
  • Suitable cyclic lactones are ⁇ -propiolactone, ⁇ -caprolactone, the alkyl derivatives of ⁇ -propiolactone and ⁇ -caprolactone, etc.
  • Suitable thiiranes are ethylene sulfide, 1,2-propylene sulphide, thioepichlorohydrin, etc.
  • Suitable thietanes are 1,3-propylene sulphide, 3,3-dimethylthietane, etc.
  • thermosetting compounds (e6) can be cured by thermal curing promoters.
  • Suitable thermal curing promotors can be selected by the skilled artisan by the nature of the reactive functional groups in the binder.
  • Suitable thermal curing promotors catalysts are e.g. sulfonium and phosphonium salts of organic or inorganic acids, imidazole and imidazole derivatives, quaternary ammonium compounds, and amines.
  • the thermal curing promotors, where desired, are preferably used in an amount of from 0.001 % by weight to about 10% by weight, based on the total weight of the polymerizable composition according to the invention.
  • the afore-mentioned compounds of the formula (I) are in particular advantageous as thermal curing promoters for radically polymerizable compositions.
  • they are used as resists to manufacture color filters for a variety of display applications and for image sensors such as charge coupled device (CCD) and complementary metal-oxide semiconductor (CMOS).
  • CCD charge coupled device
  • CMOS complementary metal-oxide semiconductor
  • the polymerizable compositions according to the invention can further be used for manufacturing spacers, which control a cell gap of the liquid crystal part in liquid crystal display panels.
  • the polymerizable compositions according to the invention are also suitable as overcoat layer for color filters and LCDs, sealants for LCDs, insulation layers for LCDs, resists or photosensitive compositions to generate structures or layers in the manufacturing processes of plasma-display panels, electroluminescence displays and LCDs, solder resists, and as a photoresist material used for forming dielectric layers in a sequential build-up layer of a printed circuit board.
  • the polymerizable composition according to the invention comprises at least one binder polymer (d), wherein component (d) is selected from alkaline developable resins.
  • Alkaline developable resins comprise functional groups that provide the resin with good alkaline solubility. They are suitable for all types of applications comprising a development step, wherein the uncured resin is dissolved in an alkaline developer solution.
  • the invention relates to a polymerizable composition
  • a polymerizable composition comprising:
  • the polymerizable composition according to the invention preferably comprises the component (b) in an amount of from about 2 to 80% by weight, more preferably from about 5 to 70% by weigth, based on the whole solid contents of the polymerizable composition (i.e. the amount of all components without the solvent(s)).
  • the acrylate monomer (b) is preferably selected from compounds that contain one or more (e.g. 1, 2, 3 or 4) acryloyl and/or methacryloyl moieties.
  • acrylate monomer encompasses also acrylate oligomers that contain one or more (e.g. 1, 2, 3 or 4) acryloyl and/or methacryloyl moieties.
  • Examples of compounds (b) containing a double bond are (meth)acrylic acid, alkyl(meth)acrylates, hydroxyalkyl(meth)acrylates or aminoalkyl(meth)acrylates.
  • Preferred compounds (b) are for example methyl(meth)acrylate, ethyl(meth)acrylate, n-butyl(meth)acrylate, isobutyl(meth)acrylate, tert-butyl(meth)acrylate, n-propyl(meth)acrylate, isopropyl(meth)acrylate, n-hexyl(meth)acrylate, cyclohexyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, isobornyl(meth)acrylate, benzyl(meth)acrylate, 2-hydroxyethyl(meth)acrylate, 2-hydroxypropyl(meth)acrylate, methoxyethyl(meth)acryl
  • compounds (b) are (meth)acrylonitrile, (meth)acrylamide, N-substituted (meth)acrylamides, vinyl esters, vinyl ethers, styrene, alkylstyrenes, hydroxystyrenes, halostyrenes, N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylacetamide, N-vinylformamide, vinyl chloride, vinylidene chloride, and mixtures thereof.
  • Suitable N-substituted (meth)acrylamides are e.g. N,N-dimethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N,N-dibutyl (meth)acrylamide, N-methyl(meth)acrylamide, N-ethyl(meth)acrylamide, N-butyl(meth)acrylamide, N-(meth)acryloylmorpholine, and mixtures thereof
  • Suitable vinyl esters are as vinyl acetate, vinyl propionate and mixtures thereof.
  • a suitable vinyl ether is isobutyl vinyl ether.
  • polyunsaturated compounds (b) of relatively high molecular mass are polyesters, polyurethanes, polyethers and polyamides, which contain ethylenically unsaturated carboxylate groups.
  • Particularly suitable examples are esters of an ethylenically unsaturated carboxylic acid with a polyol and/or polyepoxide.
  • unsaturated carboxylic acids are acrylic acid, methacrylic acid, crotonic acid, itaconic acid, cinnamic acid, and unsaturated fatty acids, such as linolenic acid or oleic acid.
  • Acrylic acid and methacrylic acid are preferred.
  • Suitable polyols are aromatic, in particular, aliphatic and cycloaliphatic polyols.
  • aromatic polyols are hydroquinone, 4,4'-dihydroxydiphenyl, 2,2-bis(4-hydroxyphenyl)methane, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxyphenyl)hexafluoropropane, 9,9-bis(4hydroxyphenyl)fluorene, novolacs and resols.
  • aliphatic and cycloaliphatic polyols are alkylenediols having preferably 2 to 12 C atoms, such as ethylene glycol, 1,2- or 1,3-propanediol, 1,2-, 1,3- or 1,4-butanediol, pentanediol, hexanediol, octanediol, dodecanediol, diethylene glycol, triethylene glcyol, polyethylene glycols having molecular weights of preferably from 200 to 1500, 1,3-cyclopentanediol, 1,2-, 1,3- or 1,4-cyclohexanediol, 1,4-dihydroxymethylcyclohexane, glycerol, triethanolamine, trimethylolethane, trimethylolpropane, pentaerythritol, pentaerythritol monooxalate, dipentaerythrito
  • polystyrene resin polystyrene resin
  • copolymers containing hydroxyl groups in the polymer chain or in side groups examples being homopolymers or copolymers comprising vinyl alcohol or comprising hydroxyalkyl (meth)acrylates.
  • polystyrene resin examples include esters and urethanes having hydroxyl end groups.
  • the polyols may be partially or completely esterified with one unsaturated carboxylic acid or with different unsaturated carboxylic acids.
  • the free hydroxyl groups may be modified, for example etherified or esterified with other carboxylic acids.
  • esters based on polyols are trimethylolpropane tri(meth)acrylate, trimethylolpropane tri(acryloyloxypropyl)ether, trimethylolethane tri(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, tetramethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol tri(meth)acrylate monooxalate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate,
  • polyepoxides are those based on the above-mentioned polyols and epichlorohydrin. Typical examples are bis(4-glycidyloxyphenyl)methane, 2,2-bis(4-glycidyloxyphenyl)propane, 2,2-bis(4-glycidyloxyphenyl)hexafluoropropane, 9,9-bis(4-glycidyloxyphenyl)fluorene, bis[4-(2-glycidyloxyethoxy)phenyl]methane, 2,2-bis[4-(2-glycidyloxyethoxy)phenyl]propane, 2,2-bis[4-(2-glycidyloxyethoxy)phenyl]hexafluoropropane, 9,9-bis[4-(2-glycidyloxyethoxy)phenyl]fluorene, bis[4-(2-glycidyloxypropoxy)phenyl]methane,
  • Typical examples based on polyepoxides are 2,2-bis[4- ⁇ (2-hydroxy-3-acryloxy)propoxy ⁇ phenyl]propane, 2,2-bis[4- ⁇ (2-hydroxy-3-acryloxy)propoxyethoxy ⁇ phenyl]propane, 9,9-bis[4- ⁇ (2-hydroxy-3-acryloxy)propoxy ⁇ phenyl]fluorene, 9,9-bis[4- ⁇ (2-hydroxy-3-acryloxy)propoxyethoxy ⁇ phenyl]fluorine, glycerol 1,3-diglycerolate diacrylate and reaction products of epoxy resins based on novolacs with (meth)acrylic acid.
  • Preferred multifunctional (meth)acrylate monomers or oligomers include pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, ditrimethylolpropane tetraacrylate, pentaerythritol triacrylate, tris(2-hydroxy ethyl) isocyanurate triacrylate.
  • a particularly preferred acrylate monomers (b) is dipentaerythritol-hexaacrylate (DPHA).
  • a further particularly preferred acrylate monomers (b) is dipentaerythritol-pentaacrylate (DPPA).
  • Examples of commercially available compounds (b) having two acryloyl or methacryloyl moietyies are Aronix®M-210, Aronix®M-240, Aronix®M-6200 (TOAGOSEI Co., LDT., KAYARAD HDDA, KAYARAD HX-220, KAYARAD HX-620, KAYARAD R-526, KAYARAD UX-2201, KAYARAD MU-2100 (NIPPON KAYAKU Co., LTD.), VISCOAT-260, VISCOAT-355HP (OSAKA ORGANIC CHEMICAL INDUSTRY LTD.).
  • Examples of commercially available compounds (b) having three or more acryloyl or methacryloyl moietyies are Aronix®M-309, Aronix®M-400, Aronix®M-1310, Aronix®M-1960, Aronix®M-7100, Aronix®M-8530, Aronix®TO-1450 (TOAGOSEI Co., LDT.), KAYARAD TMPTA, KAYARAD DPHA, KAYARAD DPCA-20, KAYARAD MAX-3510 (NIPPON KAYAKU Co., LTD.), VISCOAT-295, VISCOAT-300, VISCOAT-GPT, VISCOAT-3PA, VISCOAT-400 (OSAKA ORGANIC CHEMICAL INDUSTRY LTD.).
  • urethane acrylate monomers (b) having two or more acryloyl or methacryloyl moietyies are NEW FRONTIER R-1150 (DAI-ICHI KO-GYO SEIYAKU CO., LTD.) KAYARAD DPHA-40H, KAYARAD UX-5000 (NIPPON KAYAKU Co., LTD.), UN-9000H (Negami Chemical Industrial Co., Ltd.).
  • the choice of a suitable photoinitiator (c) is usually not critical.
  • the photoinitiator (c) is for example selected from benzophenones, bisimidazoles, aromatic ⁇ -hydroxyketones, benzylketals, aromatic ⁇ -aminoketones, phenylglyoxalic acid esters, mono-acylphosphinoxides, bis-acylphosphinoxides, tris-acylphosphinoxides, oximesters derived from aromatic ketones and/or oxime esters of the carbazol type.
  • oligomeric compounds such as for example oligomeric alpha hydroxyl ketones e.g. 2-hydroxy-1- ⁇ 1-[4-(2-hydroxy-2-methyl-propionyl)-phenyl]-1,3,3-trimethyl-indan-5-yl ⁇ -2-methyl-propan-1-one, ESACURE KIP provided by Fratelli Lamberti, or oligomeric alpha amino ketones may be employed as well.
  • oligomeric alpha hydroxyl ketones e.g. 2-hydroxy-1- ⁇ 1-[4-(2-hydroxy-2-methyl-propionyl)-phenyl]-1,3,3-trimethyl-indan-5-yl ⁇ -2-methyl-propan-1-one
  • ESACURE KIP provided by Fratelli Lamberti
  • oligomeric alpha amino ketones may be employed as well.
  • photoinitiators (c) are:
  • the polymerizable composition according to the invention preferably comprises the component (d) in an amount of from 2 to 98% by weight, more preferably from 5 to 90% by weigth, in particular from 10 to 80% by weight, based on the whole solid contents of the polymerizable composition (i.e. the amount of all components without the solvent(s)).
  • the alkaline developable resin has free carboxylic groups.
  • the acid number is preferably from 50 to 600 mg KOH/g, more preferably 100 to 300 mg KOH/g.
  • the acid numbers stated here are the acid number according to DIN EN 12634.
  • alkali developable resins are acrylic polymers having carboxylic acid function as a pendant group, such as copolymers obtained by copolymerizing an ethylenic unsaturated carboxylic acid such as (meth)acrylic acid, 2-carboxyethyl (meth)acrylic acid, 2-carboxypropyl (meth)acrylic acid, itaconic acid, citraconic acid, mesaconic acid, fumaric acid, crotonic acid, maleic acid, maleic anhydride, fumaric anhydride, citraconic acid, mesaconic acid, itaconic acid, half-ester of maleic acid, cinnamic acid, mono[2-(meth)acryloyloxyethyl] succinate, mono[2-(meth)acryloyloxyethyl] adipate, mono[2-(meth)acryloyloxyethyl] phthalate, mono[2-(meth)acryloyloxyethyl]
  • copolymers are copolymers of acrylates and methacrylates with acrylic acid or methacrylic acid and with styrene or substituted styrene, phenolic resins, for example novolak, (poly)hydroxystyrene, and copolymers of hydroxystyrene with alkyl acrylates, acrylic acid and/or methacrylic acid.
  • copolymers are copolymers of methyl (meth)acrylate/(meth)acrylic acid, copolymers of benzyl (meth)acrylate/(meth)acrylic acid, copolymers of methyl (meth)acrylate/ethyl (meth)acrylate/(meth)acrylic acid, copolymers of benzyl (meth)acrylate/(meth)acrylic acid/styrene, copolymers of benzyl (meth)acrylate/(meth)acrylic acid/hydroxyethyl (meth)acrylate, copolymers of benzyl (meth)acrylate/(meth)acrylic acid/glycidyl (meth)acrylate, copolymers of benzyl (meth)acrylate/(meth)acrylic acid/3-(methacryloyloxymethyl)oxetane, copolymers of methyl (meth)acrylate/butyl (meth)acryl
  • the alkaline developable resin (d) has preferably free carboxylic groups, which provide the compounds with good alkaline solubility.
  • functional groups that are different from carboxylic groups, in order to obtain a resin with good alkaline solubility. Examples for such groups are phenolic groups, sulfonic acid groups, anhydride groups, and combinations thereof.
  • Typical examples of the aforementioned acid anhydride are dibasic acid anhydrides such as for example maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, endo-methylenetetrahydrophthalic anhydride, methyl-endo-methylenetetrahydrophthalic anhydride, chlorendic anhydride, and methyltetrahydrophthalic anhydride.
  • dibasic acid anhydrides such as for example maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, endo-methylenetetrahydrophthalic anhydride, methyl-endo-methylenetetrahydrophthalic
  • Suitable are also aromatic polycarboxylic anhydrides, for example trimellitic anhydride, pyromelic anhydride and benzophenone tetracarboxylic dianhydride.
  • Suitable are also polycarboxylic anhydride derivatives such as 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride.
  • alkaline developable resins (d) are polymers or oligomers having at least two ethylenically unsaturated groups and at least one carboxyl function within the molecule structure, such as a resin obtained by the reaction of a saturated or unsaturated polybasic acid anhydride with a product of the reaction of an epoxy compound and an unsaturated monocarboxylic acid (for example, EB9696 from UCB Chemicals; KAYARAD TCR1025 from Nippon Kayaku Co.LTD.; NK OLIGO EA-6340, EA-7440 from Shin-Nakamura Chemical Co.,Ltd.).
  • a resin obtained by the reaction of a saturated or unsaturated polybasic acid anhydride with a product of the reaction of an epoxy compound and an unsaturated monocarboxylic acid for example, EB9696 from UCB Chemicals; KAYARAD TCR1025 from Nippon Kayaku Co.LTD.; NK OLIGO EA-6340, EA-7440 from Shin
  • binders are described in JP2002-206014A , JP2004-69754A , JP2004-302245A , JP2005-77451A , J P2005-316449A , JP2005-338328A and JP3754065B2 .
  • alkaline developable resins (d) are the above-mentioned polymers or oligomers having at least one ethylenically unsaturated groups
  • alkaline developable resins (d) are reaction products obtained by adding an epoxy group containing unsaturated compound to a part of the carboxyl groups of a carboxylic acid group containing polymer (for ex., ACA200, ACA200M, ACA210P, ACA230AA, ACA250, ACA300, ACA320 from Daicel Chemical Industries, Ltd. and Ripoxy SPC-1000 provided by Showa Highpolymer).
  • the abovementioned binder polymers which are resulting from the reaction of an unsaturated carboxylic acid compound with one or more polymerizable compounds, for example, copolymers of (meth)acrylic acid, benzyl (meth)acrylate, styrene and 2-hydroxyethyl (meth)acrylate, copolymers of (meth)acrylic acid, styrene and ⁇ -methystyrene, copolymers of (meth)acrylic acid, N-phenylmaleimide, styrene and benzyl (meth)acrylate, copolymers of (meth)acrylic acid and styrene, copolymers of (meth)acrylic acid and benzyl (meth)acrylate, copolymers of tetrahydrofurfuryl (meth)acrylate, styrene and (meth)acrylic acid and the like.
  • Examples of the unsaturated compounds having an epoxy group are given below in the formula (V-1) - (V-15); wherein R 50 is hydrogen or a methyl group, and M 3 is substituted or unsubstituted alkylene having 1 to 10 carbon atoms.
  • Among these compounds, compounds having alicyclic epoxy groups are particularly preferred, because these compounds have a high reactivity with carboxyl group-containing resins, accordingly the reaction time can be shortened. These compounds further do not cause gelation in the process of reaction and make it possible to carry out the reaction stably.
  • glycidyl acrylate and glycidyl methacrylate are advantageous from the viewpoint of sensitivity and heat resistance because they have a low molecular weight and can give a high conversion of esterification.
  • Unsaturated compounds having a hydroxy group such as 2-hydroxyethyl (meth)acrylate and glycerol mono(meth)acrylate can be used instead of the above mentioned epoxy group containing unsaturated compounds as the reactant for carboxylic acid group containing polymers.
  • half esters of anhydride containing polymers for example reaction products of a copolymer of maleic anhydride and one or more other polymerizable compounds with (meth)acrylates having an alcoholic hydroxyl group such as 2-hydroxyethyl (meth)acrylate or having an epoxy group for example such as the compounds described in the formula (V-1) - (V-15).
  • Reaction products of polymers having alcoholic hydroxyl groups such as copolymers of 2-hydroxyethyl (meth)acrylate, (meth)acrylic acid, benzyl methacylate and styrene, with (meth)acrylic acid or (meth)acryl chloride can also be used.
  • reaction products of a polyester with terminal unsaturated groups which is obtained from the reaction of a dibasic acid anhydride and a compound having at least two epoxy groups followed by further reaction with an unsaturated compound, with a polybasic acid anhydride.
  • polyimide resin having ethylenically unsaturated groups and at least one carboxyl function.
  • the polyimide binder resin in the present invention can be a polyimide precursor, for example, a poly(amic acid).
  • alkali developable resins (d) are:
  • the polymerizable composition according to the invention and in particular the polymerizable composition comprising as component (d) at least one alkaline developable resin may contain further components (e) and/or (f), as mentioned in the following:
  • Pigments and/or dyes may be present.
  • the pigments which can be comprised in the composition according to the present invention, including a pigmented color filter resist composition, are preferably processed pigments.
  • the red pigment comprises, for example, an anthraquinone type pigment alone, a dike-topyrolopyrole type pigment alone, a mixture of them or a mixture consisting of at least one of them and a disazo type yellow pigment or an isoindoline type yellow pigment, in particular C. I. Pigment Red 177 alone, C. I. Pigment Red 254 alone, a mixture of C. I. Pigment Red 177 and C. I. Pigment Red 254 or a mixture consisting of at least one member of C. I. Pigment Red 177, C.
  • C.I. refers to the Color Index, known to the person skilled in the art and publicly available).
  • Further suitable examples for the pigment are C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 168, 176, 179, 180, 185, 202, 207, 209, 214, 222, 244, 255, 264, 272 and C.I.
  • Examples of the dyes for red color are C. I. Solvent Red 25, 27, 30, 35, 49, 83, 89, 100, 122, 138, 149, 150, 160, 179, 218, 230, C. I. Direct Red 20, 37, 39, 44, and C. I.
  • the Red dyes can be used in combination with yellow and/or orange dyes.
  • the green pigment comprises for instance a halogenated phthalocyanine type pigment alone or its mixture with a bisazo type yellow pigment, an quinophthalone type yellow pigment or a metal complex, in particular C. I. Pigment Green 7 alone, C. I. Pigment Green 36 alone, C. I. Pigment 58 alone, or a mixture consisting of at least one member of C. I. Pigment Green 7, C. I. Pigment Green 36, Pigment Green 58 and C. I. Pigment Yellow 83, C. I. Pigment Yellow 138 or C. I. Pigment Yellow 150.
  • Other suitable green pigments are C.I. Pigment Green 15, 25 and 37. Examples for suitable green dyes are C. I. Acid Green 3, 9, 16, C. I. Basic Green 1 and 4.
  • the blue dye comprises, for example, a methine type dye, an anthraquinone type dye, an azo type dye, a metal complex azo type dye, a triarylmethane type dye or a phthalocyanine type dye.
  • suitable blue pigments are phthalocyanine type pigments, used either alone or in combination with an dioxazine type violet pigment, for instance, C. I. Pigment Blue 15:6 alone, a combination of C. I. Pigment Blue 15:6 and C. I. Pigment Violet 23.
  • Further examples for blue pigments are such of C. I. Pigment Blue 15:3, 15:4, 16, 22, 28 and 60.
  • Other suitable pigments are C. I. Pigment Violet 14,19, 23, 29, 32, 37, 177 and C. I.
  • Orange 73 examples are C. I. Solvent Blue 11, 25, 37, 45, 49, 68, 78, 94, C. I. Direct Blue 25, 86, 90, 108, C. I. Acid Blue 1, 3, 7, 9, 15, 83, 90, 103, 104, 158, 161, C. I. Basic Blue 1, 3, 7, 9, 25, 105, C. I. Disperse Blue 198 and Mordant Blue 1.
  • the pigment of the photopolymeric composition for black matrix preferably comprises at least one member selected from the group consisting of carbon black, titanium black, iron oxide, lactone, lactam and perylene.
  • Preferred example is carbon black.
  • a mixture of other pigments which, in total, give the black appearance can also be used.
  • C. I. Pigment Black 1, 7, 31 and 32 can be used alone or in combination.
  • dyes used for color filter are C. I. Solvent Yellow 2, 5, 14, 15, 16, 19, 21, 33, 56, 62, 77, 83, 93, 162, 104, 105, 114, 129, 130, 162, C. I. Disperse Yellow 3, 4, 7, 31, 54, 61, 201, C. I. Direct Yellow 1, 11, 12, 28, C. I. Acid Yellow 1, 3, 11, 17, 23, 38, 40, 42, 76, 98, C. I. Basic Yellow 1, C. I. Solvent Violet 13, 33, 45, 46, C. I. Disperse Violet 22, 24, 26, 28, 31, C. I. Acid Violet 49, C. I. Basic Violet 2, 7, 10, C. I. Solvent Orange 1, 2, 5, 6, 37, 45, 62, 99, C. I.
  • Acid Orange 1 7, 8, 10, 20, 24, 28, 33, 56, 74, C. I. Direct Orange 1, C. I. Disperse Orange 5, C. I. Direct Brown 6, 58, 95, 101, 173, C. I. Acid Brown 14, C. I. Solvent Black 3, 5, 7, 27, 28, 29, 35, 45 and 46.
  • color filters complementary colors, yellow, magenta, cyan and optionally green, are used instead of red, green and blue.
  • yellow for this type of color filters, the abovementioned yellow pigments and dyes can be employed.
  • the colorants suitable for magenta color are C. I. Pigment Red 122, 144, 146, 169, 177, C. I. Pigment Violet 19 and 23.
  • cyan color are aluminum phthalocyanine pigments, titanium phthalocyanine pigments, cobalt phthalocyanine pigments, and tin phthalocyanine pigments.
  • the pigments in the color filter resist composition have preferably a mean particle diameter smaller than the wavelength of visible light (400 nm to 700 nm). Particularly preferred is a mean pigment diameter of ⁇ 100 nm.
  • the concentration of the pigment in the total solid component is for example in the range of 5% to 80% by weight, in particular in the range of 20% to 65 % by weight.
  • the concentration of the dye in the total solid component is for example in the range of 0.5 % to 95 % by weight, in particular in the range of 0.5% to 70% by weight.
  • the pigments may be stabilized in the photosensitive composition by pretreatment of the pigments with a dispersant to improve the dispersion stability of the pigment in the liquid formulation. Suitable additives are described below.
  • Additives are optional present such as dispersing agents, surfactant, adhesion promoters, photosensitizer and the like.
  • the surface treatment reagents are, for example, surfactants, polymeric dispersants, general texture improving agents, pigment derivatives and mixtures thereof. It is especially preferred when the colorant composition according to the invention comprises at least one polymeric dispersant and/or at least pigment derivative.
  • Suitable surfactants include anionic surfactants such as alkylbenzene- or alkylnahthalene-sulfonates, alkylsulfosuccinates or naphthalene formaldehyde sulfonates; cationic surfactants including, for example, quaternary salts such as benzyl tributyl ammonium chloride; or nonionic or amphoteric surfactants such as polyoxyethylene surfactants and alkyl- or amidopropyl betaines, respectively.
  • anionic surfactants such as alkylbenzene- or alkylnahthalene-sulfonates, alkylsulfosuccinates or naphthalene formaldehyde sulfonates
  • cationic surfactants including, for example, quaternary salts such as benzyl tributyl ammonium chloride
  • nonionic or amphoteric surfactants such as polyoxyethylene surfactants and al
  • Illustrative examples of the surfactant include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether and polyoxyethylene oleyl ether; polyoxyethylene alkylphenyl ethers such as polyoxyethylene octylphenyl ether and polyoxyethylene nonylphenyl ether; polyethylene glycol diesters such as polyethylene glycol dilaurate and polyethylene glycol distearate; sorbitan fatty acid esters; fatty acid modified polyesters; tertiary amine modified polyurethanes; polyethyleneimines; those available under the trade names of KP (a product of Shin-Etsu Chemical Co., Ltd), Polyflow (a product of KYOEISHA CHEMICAL Co., Ltd), F-Top (a product of Tochem Products Co., Ltd), MEGAFAC (a product of Dainippon Ink & Chemicals, Inc.), Fluorad (a product of Sumitomo 3M Ltd), As
  • surfactants may be used alone or in admixture of two or more.
  • the surfactant is generally used in an amount of 50 parts or less by weight, preferably 0 to 30 parts by weight, based on 100 parts by weight of the colorant composition.
  • Polymeric dispersants include high molecular weight polymers with pigment affinic groups. Examples are: statistical co-polymers comprised from, for instance, styrene derivatives, (meth)acrylates and (meth)acrylamides, and such statistical co-polymers modified by post modification; block co-polymers and/or comb polymers comprised from, for instance, styrene derivatives, (meth)acrylates and (meth)acrylamides, and such block co-polymers and/or comb polymers modified by post modification; polyethylenimines, which for instance is crafted with polyesters; polyamines, which for instance is crafted with polyesters; and many kinds of (modified) polyurethanes.
  • statistical co-polymers comprised from, for instance, styrene derivatives, (meth)acrylates and (meth)acrylamides, and such statistical co-polymers modified by post modification
  • block co-polymers and/or comb polymers comprised from, for
  • Polymeric dispersants may also be employed. Suitable polymeric dispersants are, for example, BYK' s DISPERBYK® 101, 115, 130, 140, 160, 161, 162, 163, 164, 166, 168, 169, 170, 171, 180, 182, 2000, 2001, 2009, 2020, 2025, 2050, 2090, 2091, 2095, 2096, 2150, Ciba' s Ciba® EFKA® 4008, 4009, 4010, 4015, 4046, 4047, 4050, 4055, 4060, 4080, 4300, 4310, 4330, 4340, 4400, 4401, 4402, 4403, 4406, 4500, 4510, 4520, 4530, 4540, 4550, 4560, Ajinomoto Fine Techno's PB®711, 821, 822, 823, 824, 827, Lubrizol' s SOLSPERSE® 1320, 13940, 17000, 20000, 21000, 24000, 26000
  • Suitable texture improving agents are, for example, fatty acids such as stearic acid or behenic acid, and fatty amines such as laurylamine and stearylamine.
  • fatty alcohols or ethoxylated fatty alcohols, polyols such as aliphatic 1,2-diols or epoxidized soy bean oil, waxes, resin acids and resin acid salts may be used for this purpose.
  • Suitable pigment derivatives are, for example, copper phthalocyanine derivatives such as Ciba' s Ciba® EFKA® 6745, Lubrizol' s SOLSPERSE® 5000, 12000, BYK' s SYNERGIST 2100 and azo derivatives such as Ciba® EFKA® 6750, SOLSPERSE® 22000 and SYNERGIST 2105.
  • copper phthalocyanine derivatives such as Ciba' s Ciba® EFKA® 6745, Lubrizol' s SOLSPERSE® 5000, 12000, BYK' s SYNERGIST 2100
  • azo derivatives such as Ciba® EFKA® 6750, SOLSPERSE® 22000 and SYNERGIST 2105.
  • compositions of the present invention which are used as resist formulations, in particular in color filter formulations.
  • Subject of the invention also is a photopolymerizable composition as described above as further additive comprising a dispersant or a mixture of dispersants as well as a photopolymerizable composition as described above as further additive comprising a pigment or a mixture of pigments.
  • the content of the dispersing agent is preferably from 1 to 80% by mass, more preferably from 5 to 70% by mass, even more preferably from 10 to 60% by mass, based on the mass of the pigment.
  • the curable composition of the invention may contain an adhesion improving agent for increasing adhesion to a hard surface, such as of a support.
  • the adhesion improving agent may be a silane coupling agent, a titanium coupling agent or the like.
  • Photopolymerization can also be accelerated by adding further photosensitizers or coinitiators which shift or broaden the spectral sensitivity.
  • photosensitizers or coinitiators which shift or broaden the spectral sensitivity.
  • aromatic compounds for example benzophenone and derivatives thereof, thioxanthone and derivatives thereof, anthraquinone and derivatives thereof, coumarin and phenothiazine and derivatives thereof, and also 3-(aroylmethylene)thiazolines, rhodanine, camphorquinone, but also eosine, rhodamine, erythrosine, xanthene, thioxanthene, acridine, e.g. 9-phenylacridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinyl)pentane, cyanine and merocyanine dyes.
  • a photosensitizer may be selected from the group consisting of benzophenone and its derivatives, thioxanthone and its derivatives, anthraquinone and its derivatives, or coumarin and its derivatives.
  • amines for example triethanolamine, N-methyldiethanolamine, ethyl-p-dimethylaminobenzoate, 2-(dimethylamino)ethyl benzoate, 2-ethylhexyl-p-dimethylaminobenzoate, octyl-para-N,N-dimethylaminobenzoate, N-(2-hydroxyethyl)-N-methyl-para-toluidine or Michler's ketone.
  • the action of the amines can be intensified by the addition of aromatic ketones of the benzophenone type.
  • amines which can be used as oxygen scavengers are substituted N,N-dialkylanilines, as are described in EP339841 .
  • Other accelerators, coinitiators and autoxidizers are thiols, thioethers, disulfides, phosphonium salts, phosphine oxides or phosphines, as described, for example, in EP438123 , in GB2180358 and in JP Kokai Hei 6-68309 .
  • additive(s) The choice of additive(s) is made depending on the field of application and on properties required for this field.
  • the additives described above are customary in the art and accordingly are added in amounts which are usual in the respective application.
  • Thermal inhibitors are intended to prevent premature polymerization, examples being hydroquinone, hydroquinone derivatives, p-methoxyphenol, ⁇ -naphthol or sterically hindered phenols, such as 2,6-di-tert-butyl-p-cresol.
  • copper compounds such as copper naphthenate, stearate or octoate
  • phosphorus compounds for example triphenylphosphine, tributylphosphine, triethylphosphine, triphenyl phosphate or tribenzyl phosphate
  • quaternary ammonium compounds for example tetramethylammonium chloride or trimethylbenzylammonium chloride
  • hydroxylamine derivatives for example N-diethylhydroxylamine.
  • UV absorbers which can be added in a small quantity are UV absorbers, for example those of the hydroxyphenylbenzotriazole, hydroxyphenyl-benzophenone, oxalamide or hydroxyphenyl-s-triazine type. These compounds can be used individually or in mixtures, with or without sterically hindered amines (HALS).
  • HALS sterically hindered amines
  • Suitable solvents are ketones, ethers and esters, such as methyl ethyl ketone, isobutyl methyl ketone, cyclopentanone, cyclohexanone, N-methylpyrrolidone, dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dipropyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol dipropyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether,
  • compositions according to this invention can comprise additionally a crosslinking agent which is activated by an acid or a base, for example as described in JP 10 221843-A , and a compound which generates acid or base thermally or by actinic radiation and which activates a crosslinking reaction.
  • cationic photo or thermal initiators such as sulfonium-, phosphonium- or iodonium salts, for example IRGACURE® 250, San-Aid SI series, SI-60L, SI-80L, SI-100L, SI-110L, SI-145, SI-150, SI-160, SI-180L produced by Sanshin Chemical, cyclopentadienyl-arene-iron(II) complex salts, for example ( ⁇ 6 -isopropylbenzene)( ⁇ 5 -cyclopentadienyl)iron(II) hexafluorophosphate, as well as oxime sulfonic acid esters, for example described in EP 780729 .
  • sulfonium-, phosphonium- or iodonium salts for example IRGACURE® 250, San-Aid SI series, SI-60L, SI-80L, SI-100L, SI-110L, SI-145, SI-150, SI-
  • pyridinium and (iso)quinolinium salts as described e.g. in EP 497531 and EP 441232 may be used in combination with the new photoinitiators.
  • bases are imidazole and its derivatives for example Curezole OR series and CN series provided by Shikoku Chemicals.
  • the crosslinking agents which can be activated by acid or base include compounds having epoxy or oxetane groups. There may be used a solid or liquid known epoxy or oxetane compound and said compound is used depending on required characteristics.
  • a preferred epoxy resin is a bisphenol S type epoxy resin such as BPS-200 produced by Nippon Kayaku Co., Ltd., EPX-30 produced by ACR Co., Epiculon EXA-1514 produced by Dainippon Ink & Chemicals Inc., etc.; a bisphenol A type epoxy resin such as Epiculon N-3050, N-7050, N-9050 produced by Dainippon Ink & Chemicals Inc., XAC-5005, GT-7004, 6484T, 6099; a bisphenol F type epoxy resin such as YDF-2004, YDF2007 produced by Tohto Kasei Co., etc.; a bisphenol fluorene type epoxy resin such as OGSOL PG, PG-100, EG, EG-210 produced by O
  • oxetane compounds are 3-ethyl-3-hydroxymethyloxetane (oxetane alcohol), 2-ethylhexyloxetane, xylene bisoxetane, 3-ethyl-3[[(3-ethyloxetane-3-yl)methoxy]methyl]oxetane (Aron Oxetane series) provided by Toagosei.
  • compositions according to the invention comprising at least one compound of the formula I are especially suitable for the following applications:
  • compositions according to the invention comprising at least one compound of the formula I are also suitable for the following applications:
  • the invention further relates to the use of the photoresist composition to manufacture color filters for a variety of display applications and for image sensors such as charge coupled device (CCD) and complementary metal-oxide semiconductor (CMOS), spacers for LCD, overcoat layer for color filter and LCD, sealant for LCD, optical films for a variety of display applications, insulation layer for LCD, resists or photosensitive compositions to generate structures or layers in the manufacturing processes of plasma-display panels, electroluminescence displays and LCD, solder resists, as a photoresist material used for forming dielectric layers in a sequential build-up layer of a printed circuit board.
  • CCD charge coupled device
  • CMOS complementary metal-oxide semiconductor
  • compositions according to the invention are particularly suitable for the production of color filters or color mosaic systems, such as described, for example, in EP 320 264.
  • the color filters can be used, for example, for flat panel display technology such as LCD, electroluminescent display and plasma display, for image sensors such as CCD and CMOS, and the like.
  • the color filters usually are prepared by forming red, green and blue pixels and black matrix on a glass substrate.
  • photocurable compositions according to the invention can be employed.
  • a particularly preferred method of use comprises adding of the coloring matters, dyes and pigments of red, green and blue colors to the light-sensitive resin composition of the present invention, coating of the substrate with the composition, drying of the coating with a short heat treatment, patternwise exposure of the coating (i.e. through a suitable mask) to actinic radiation and subsequent development of the pattern in a suitable aqueous alkaline developer solution and a heat treatment.
  • a red, green, blue and black pigmented coating in any desired order, on top of each other with this process a color filter layer with red, green and blue color pixels and black matrix can be produced.
  • suitable radiation from about 150 nm to 600 nm, for example 190-600 nm (UV-VIS region) is chosen, for example, in sunlight or light from artificial light sources. Consequently, a large number of very different types of light sources are employed. Both point sources and arrays ("lamp carpets") are suitable. Examples are carbon arc lamps, xenon arc lamps, super high-, high-, medium- and low-pressure mercury lamps, possibly with metal halide dopes (metal-halogen lamps), microwave-stimulated metal vapor lamps, excimer lamps, superactinic fluorescent tubes, fluorescent lamps, argon incandescent lamps, electronic flashlights, photographic flood lamps, light emitting diodes (LED), electron beams and X-rays.
  • LED light emitting diodes
  • the distance between the lamp and the substrate to be exposed in accordance with the invention may vary depending on the intended application and the type and output of lamp, and may be, for example, from 2 cm to 150 cm.
  • Laser light sources for example excimer lasers, such as KrF lasers for example at 248 nm, ArF-lasers for example at 193 nm and F 2 lasers for exposure at 157 nm are also suitable. Lasers in the visible region can also be employed.
  • the light-sensitive resin composition of the present invention can be used as well for a layer transfer material. That is, the light-sensitive resin composition is layer-wise provided directly on a temporary support, preferably on a polyethylene terephthalate film, or on a polyethylene terephthalate film on which an oxygen-shielding layer and a peeling layer or the peeling layer and the oxygen-shielding layer are provided. Usually, a removable cover sheet made of a synthetic resin is laminated thereon for a protection in handling. Further, there can be applied as well a layer structure in which an alkali soluble thermoplastic resin layer and an intermediate layer are provided on a temporary support and further a light-sensitive resin composition layer is provided thereon ( JP 5-173320-A ).
  • the above cover sheet is removed in use and the light-sensitive resin composition layer is laminated on a permanent support. Subsequently, peeling is carried out between those layer and a temporary support when an oxygen-shielding layer and a peeling layer are provided, between the peeling layer and the oxygen-shielding layer when the peeling layer and the oxygen-shielding layer are provided, and between the temporary support and the light-sensitive resin composition layer when either the peeling layer or the oxygen-shielding layer is not provided, and the temporary support is removed.
  • the developer solution can be used in all forms known to the person skilled in the art, for example in form of a bath solution, puddle, or a spraying solution.
  • the methods such as rubbing with a rotary brush and rubbing with a wet sponge.
  • the temperature of the developing solution is preferably at and around room temperature to 40°C.
  • the developing time is changeable according to the specific kind of the light-sensitive resin composition, the alkalinity and temperature of the developing solution, and the kind and concentration of the organic solvent in the case where it is added. Usually, it is 10 seconds to 2 minutes. It is possible to put a rinsing step after the development processing.
  • a final heat treatment is preferably carried out after the development processing.
  • a support having a layer which is photopolymerized by exposing (hereinafter referred to as a photocured layer) is heated in an electric furnace and a drier, or the photocured layer is irradiated with an infrared lamp or heated on a hot plate.
  • the heating temperature and time depend on the composition used and the thickness of the formed layer. In general, heating is preferably applied at about 120°C to about 250°C, for about 2 to about 60 minutes.
  • an inorganic black matrix can be formed from deposited (i.e. sputtered) metal (i.e. chromium) film on the transparent substrate by a suitable imaging process, for example utilizing photolithographic patterning by means of an etch resist, etching the inorganic layer in the areas not protected by the etch resist and then removing the remaining etch resist.
  • the photosensitive or thermosetting composition of the present invention can also be used to form such overcoat layers, because a cured film of the composition is excellent in flatness, hardness, chemical and thermal resistance, transparency especially in a visible region, adhesion to a substrate, and suitability for forming a transparent conductive film, e.g., an ITO film, thereon.
  • a protective layer In the production of a protective layer, there has been a demand that unnecessary parts of the protective layer, for example on scribing lines for cutting the substrate and on bonding pads of solid image sensors should be removed from the substrate as described in JP57-42009-A , JP1-130103-A and JP1-134306-A . In this regard, it is difficult to selectively form a protective layer with good precision using the above-mentioned thermosetting resins.
  • the photosensitive composition allows to easily remove the unnecessary parts of the protective layer by photolithography.
  • the photosensitive compositions according to the invention can further be used for manufacturing spacers, which control a cell gap of the liquid crystal part in liquid crystal display panels. Since the properties of light transmitted or reflected through the liquid crystal layer in a liquid crystal display are dependent on the cell gap, the thickness accuracy and uniformity over the pixel array are critical parameters for the performance of the liquid crystal display unit.
  • columns of a resin can be formed as spacers in the region between the pixel array region and the counter electrode to form a prescribed cell gap.
  • Photosensitive materials having adhesive properties with photolithography are commonly used, for instance, in the manufacturing process of color filters. This method is advantageous compared with the conventional method using spacer beads in the points that location, number and height of the spacers may be controlled freely. In a color liquid crystal display panel, such spacers are formed in the non-imaging area under black matrix of color filter elements. Therefore, the spacers formed using photosensitive compositions do not decrease brightness and optical aperture.
  • Photosensitive compositions for producing protective layer with spacers for color filters are disclosed in JP 2000-81701-A and dry film type photoresists for spacer materials are also disclosed in JP 11-174459-A and JP 11-174464-A .
  • the photosensitive compositions, liquid and dry film photoresists are comprising at least an alkaline or acid soluble binder polymer, a radically polymerizable monomer, and a curing promoter.
  • thermally crosslinkable components such as epoxide and carboxylic acid may additionally be included.
  • the steps to form spacers using a photosensitive composition are as follows: a photosensitive composition is applied to the substrate, for instance a color filter panel and after the substrate is prebaked, it is exposed to light through a mask. Then, the substrate is developed with a developer and patterned to form the desired spacers. When the composition contains some thermosetting components, usually a post-baking is carried out to thermally cure the composition.
  • the photocurable compositions according to the invention are suitable for producing spacers for liquid crystal displays (as described above).
  • compositions according to the invention are also suitable for manufacturing interlayer insulating layers or dielectric layers in a liquid crystal display, and more particularly in specific LCD structures such as color filter on array type and reflection type LCDs.
  • compositions according to the invention are also suitable for insulative electrical machinery to coat the windings and seal the stator windings of electrical inductive devices, such as motors, are wound with magnet wire having enamel or other insulative coating from the environment.
  • the photosensitive thermosetting resin composition and a method of forming a solder resist pattern by the use thereof and more particularly relates to a novel photosensitive thermosetting resin composition useful as materials for the production of printed circuit boards, the precision fabrication of metallic articles, the etching of glass and stone articles, the relief of plastic articles, and the preparation of printing plates and particularly useful as a solder resist for printed circuit boards and to a method of forming a solder resist pattern by the steps of exposing a layer of the resin composition selectively to an actinic ray through a photomask having a pattern and developing the unexposed part of the layer.
  • the solder resist is a substance which is used during the soldering of a given part to a printed circuit board for the purpose of preventing molten solder from adhering to irrelevant portions and protecting circuites. It is, therefore, required to possess such properties as high adhesion, insulation resistance, resistance to soldering temperature, resistance to solvents, resistance to solvents, resistance to alkalis, resistance to acids, and resistance to plating.
  • Subject of the invention also is a solder resist comprising a composition as described above.
  • compositions comprising thermosetting elements described as compound according to the invention, in an image-forming process, e.g. a process for the preparation of solder masks, wherein
  • This process is another object of the invention.
  • the heating step (6) usually is carried out at temperature of at least 100°C and not more than 200°C, preferably at temperatures of 130 - 170°C, e.g. at 150°C.
  • the photosensitive or thermosetting coating composition of the present invention can also be used to form such coating layers, which is required adherence property, thermal resistance, flexibility, adhesiveness, electrical insulating property and humidity resistance for building, building materials, automobile parts, electrical instrument, precision instrument and the like.
  • compositions according to the invention are also suitable for dental materials are also disclosed in US6410612 and JP60011409 .
  • the photosensitive or thermosetting compositions comprise some kind of acrylic resin and polymerization initiator.
  • An anisotropic conductive adhesive is a circuit connecting material, in which conductive particles are dispersed in an insulating adhesive component, which adheres mechanically circuits disposed in the opposite direction, and simultaneously interposes a conductive particle between the circuit electrodes to establish an electrical connection.
  • an insulating adhesive component a thermoplastic resin and a thermosetting resin are usable, and the thermosetting resin is more preferably used in terms of connection reliability.
  • thermosetting resin as an adhesive component
  • a connection is made by interposing an anisotropic conductive adhesive between connected to be members, which is then heat-compressed.
  • the invention provides compositions for producing pigmented and non-pigmented paints and varnishes, powder coatings, printing inks, printing plates, adhesives, dental compositions.
  • Photoresists for electronics like electroplating resist, etch resist, both liquid and dry films, solder resist, as resists to manufacture color filters for a variety of display applications or to generate structures in the manufacturing processes of plasma-display panels (c.g. barrier rib, phosphor layer, electrode), electroluminescence, displays and LCD) (e.g.
  • Interlayer insulating layer, spacers, microlens array as composition for encapsulating electrical and electronic components, for producing magnetic recording materials, micromechanical parts, waveguides, optical switches, plating masks, etch masks, color proofing systems, glass fiber cable coatings, screen printing stencils, for producing three-dimensional objects by means of stereo-lithography, and as image recording material, especially for holographic recordings, microelectronic circuits, decolorizing materials, decolorizing materials for image recording materials, for image recording materials using microcapsules.
  • the title compound was prepared by the procedure given for example 1.2.
  • the title compound was obtained as white powder.
  • the title compound was prepared by the procedure given for example 14.2. The title compound was obtained as white powder.
  • the intermediate compound I13 was prepared by the procedure given for example 1.1 by reacting with 4-methanethioacetyl benzylmercaptan in place of p-toluenethiol. I13 was obtained as light yellow resin.
  • the intermediate compound I14 was prepared by the procedure given for example 1.2 by reacting with benzylsulfonyl chloride in place of p -toluenesulfonyl chloride. I14 was obtained as colrless resin.
  • the intermediate compound I16 was prepared by the procedure given for example 1.1. I16 was obtained as white solid.
  • the intermediate compound I10 was prepared by the procedure given for example 1.1 by reacting with 6-acetylthiohexanethiol in place of p -toluenethiol. I10 was obtained as light yellow solid.
  • the title compound was prepared by the procedure given for example 1.2.
  • the title compound was obtained as white solid.
  • the title compound was prepared by the procedure given for example 1.2.
  • the title compound was obtained as yellow resin.
  • the title compound was prepared from the intermediate compound I19 from example of 146.2 by the procedure given for example 1.2.
  • the title compound was obtained as yellow resin.
  • a blue pigment dispersion was prepared by mixing the following components and dispersing them by using a Paint conditioner (SKANDEX).
  • Blue dispersion 5.3 parts by weight blue pigment (PB15:6, Blue E provided by Toyo Ink) 1.9 parts by weight dispersant (Ajisper PB821 provided by Ajinomoto Fine Techno) 0.2 parts by weight synergist (Solsperse S5000 provided by Lubrizol) 55.8 parts by weight solvent propylene glycol monomethylether acetate (PGMEA)
  • Color filter resist blue was prepared by further adding the following components to the above dispersion prepared. 19.1 parts by weight alkaline developable binder, 37.8 % solution (Ripoxy SPC-2000, provided by Showa Highpolymer) 12.3 parts by weight solvent PGMEA 5.3 parts by weight multifunctional acrylate (DPHA, provided by UCB Chemicals)
  • the oxime sulfonate to be tested and additionally Ciba® IRGACURE® 369 (4.8 wt% in solid) as photoinitiator were added to the above color filter resist composition and mixed.
  • the composition was applied to a silicon wafer using a spin coater (1H-DX2, MIKASA). The solvent was removed by heating at 90 °C for 2.5 min in a convection oven. The thickness of the dry film was approximately 1.0 ⁇ m. Exposure was then carried out using a 250 W super high pressure mercury lamp (USHIO, USH-250BY) at a distance of 15 cm.
  • the total exposure dose determined by measuring light intensity with an optical power meter was 150 mJ/cm 2 .
  • the coating was further baked under the conditions listed in Table II below.
  • the conversion of acrylic group in baking was determined by measuring IR absorption at 810 cm -1 with a FT-IR spectrometer (FT-720, HORIBA) before and after baking.
  • the concentration of the oxime sulfonate in the composition was 0.02 mol/kg. The results of the tests were given in Table II.
  • Example 2 0.02 180 °C for 30 min 71.2
  • Example 3 0.02 180 °C for 30 min 63.4
  • Example 4 0.02 180 °C for 30 min 69.1
  • Example 5 0.02 180 °C for 30 min 72.8
  • Example 6 0.02 180 °C for 30 min 72.7
  • Example 7 0.02 180 °C for 30 min 65.5
  • Example 9 0.02 180 °C for 30 min 76.7
  • Example 10 0.02 180 °C for 30 min 70.3
  • Example 11 0.02 180 °C for 30 min 71.9
  • Example 12 0.02 180 °C for 30 min 66.6
  • Example 14 0.02 180 °C for 30 min 66.0
  • Example 17 0.02 180 °C for 30 min 75.9
  • Example 19 0.02 180 °C for 30 min 77.5
  • Example 20 0.02 180 °C for 30 min 73.8
  • Example 21 0.02 180 °C for 30 min 68.3
  • Example 22 0.02 180 °C for 30 min 73.9
  • Example 25 0.02 180 °C for
  • a blue pigment dispersion was prepared by mixing the following components and dispersing them by using a Paint conditioner (SKANDEX).
  • Blue dispersion 5.3 parts by weight blue pigment (PB15:6, Blue E provided by Toyo Ink) 1.9 parts by weight dispersant (Ajisper PB821 provided by Ajinomoto Fine Techno) 0.2 parts by weight synergist (Solsperse S5000 provided by Lubrizol) 55.8 parts by weight solvent propylene glycol monomethylether acetate (PGMEA)
  • Color filter resist blue was prepared by further adding the following components to the above dispersion prepared. 19.1 parts by weight alkaline developable binder, 37.8 % solution (Ripoxy SPC-2000, provided by Showa Highpolymer) 12.3 parts by weight solvent PGMEA 5.3 parts by weight multifunctional acrylate (DPHA, provided by UCB Chemicals)
  • the oxime sulfonate to be tested and additionally IRGACURE® 369 (4.8 wt% in solid) as photoinitiator were added to the above color filter resist composition and mixed.
  • the concentration of the oxime sulfonate in the composition was 0.02 mol/kg.
  • the composition was applied to a 2x3 cm silicon wafer using a spin coater (1H-DX2, MIKASA). The solvent was removed by heating at 90 °C for 2.5 min in a convection oven. The thickness of the dry film was approximately 1.0 ⁇ m. Exposure was then carried out using a 250 W super high pressure mercury lamp (USHIO, USH-250BY) at a distance of 15 cm.
  • the total exposure dose determined by measuring light intensity with an optical power meter was 150 mJ/cm 2 .
  • the coating was further baked under the conditions listed in Table III below.
  • the coating after baking was dipped in 12g N-methylpyrrolidone (NMP) in a glass vessel for 3 min and then leaching of the blue pigment was assessed by visual analysis of NMP layer. It was taken as "-” that leaching of blue pigment was observed, and it was taken as "+” that leaching of blue pigment was not observed.
  • NMP N-methylpyrrolidone
  • Table III Oxime sulfonate Concentration of oxime sulfonate (mol/kg in composition) Baking conditions Leaching of blue pigment - - 180 °C for 30 min - - - 230 °C for 5 min - Example 1 0.02 180 °C for 30 min + Example 16 0.02 180 °C for 30 min + Example 17 0.02 180 °C for 30 min + Example 21 0.02 180 °C for 30 min + Example 23 0.02 180 °C for 30 min + Example 37 0.02 180 °C for 30 min + Example 42 0.02 180 °C for 30 min + Example 46 0.02 180 °C for 30 min + Example 50 0.02 180 °C for 30 min + Example 53 0.02 180 °C for 30 min + Example 74 0.02 180 °C for 30 min + Example 78 0.02 180 °C for 30 min + Example 85 0.02 180 °C for 30 min + Example 86 0.02 180 °C for 30 min + Example 93 0.02 180 °C for 30 min + Example 94 0.02 180
  • the oxime sulfonate to be tested was added to a solution of above formulation and mixed.
  • the mixture was applied to a silicon wafer using a spin coater (1H-DX2, MIKASA).
  • the solvent was removed by heating at 90 °C for 2.5 min in a convection oven.
  • the thickness of the dry film was approximately 0.6 ⁇ m.
  • the coating was further baked under the conditions listed in Table III. The conversion of acrylic double bond in baking was determined by the method described above. The results of the tests are given in Table IV.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Manufacturing & Machinery (AREA)
  • Polymerisation Methods In General (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyrane Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Optical Filters (AREA)
  • Polymerization Catalysts (AREA)

Claims (16)

  1. Composition polymérisable comprenant
    (a) au moins un composé de sulfonate d'oxime de formule I

            QAaBbCc     (I)

    où a vaut 0, 1, 2, 3, 4 ou 6 ;
    b vaut 0, 1, 2, 3, 4 ou 6 ; et
    c vaut 0, 1, 2, 3, 4 ou 6 ;
    où la somme de a+b+c vaut 1, 2, 3, 4 ou 6
    où A est un groupement
    Figure imgb0330
    B est un groupement
    Figure imgb0331
    C est un groupement
    Figure imgb0332
     où # désigne le point de fixation à Q ;
    X est S, SO2 ou NR14;
    Q si a vaut 1, b vaut 0 et c vaut 0,
    est un radical R1 ; ou
    Q si a vaut 2, b vaut 0 et c vaut 0
    est un bras de liaison divalent qui est choisi parmi L-C1-C30-alkylène-L, L-C2-C30-alcénylène-L, L-C3-C16-cycloalkylène-L, L-hétérocycloalkylène-L, L-C6-C20-arylène-L, L-hétéroarylène-L, L-C1-C30-alkylène-L2-L, L-C2-C30-alcénylène-L2-L, L-C3-C16-cycloalkylène-L1-C3-C16-cycloalkylène-L, L-C3-C16-cycloalkylène-L1-hétérocycloalkylène-L, L-C3-C16-cycloalkylène-L1-C6-C20-arylène-L, L-C3-C16-cycloalkylène-L1-hétéroarylène-L, L-C6-C20-arylène-L-C6-C20-arylène-L, L-C6-C20-arylène-L1-hétéroarylène-L, L-hétéroarylène-L1-hétéroarylène-L, L-C3-C16-cycloalkylène-L1-L3-L1-C3-C16-cycloalkylène-L, L-C3-C16-cyclo-alkylène-L1-L3-L1-hétérocycloalkylène-L, L-C3-C16-cycloalkylène-L1-L3-L1-C6-C20-arylène-L, L-C3-C16-cycloalkylène-L1-L3-L1-hétéroarylène-L, L-C6-C20-arylène-L1-L3-L1-C6-C20-arylène-L, L-C6-C20-arylène-L1-L3-L1-hétéroarylène-L, et L-hétéroarylène-L1-L3-L1-hétéroarylène-L, où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements L4 non adjacents identiques ou différents, et/ou peuvent porter un ou plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arylène et chaque hétéroarylène peuvent porter un ou plusieurs radicaux RQc identiques ou différents,
    où
    L est choisi indépendamment les uns des autres parmi une liaison simple, C(S)O, C(S)NR12 ;
    L1 est indépendamment les uns des autres une liaison simple, O, S, NR14, CO, OC(O), C(O)O, C(S)O, OC(S), C(O)NR10, NR10C(O), C(S)NR12, NR12C(S) et NR10SO2 ;
    L2 est C3-C20-cycloalkylène, hétérocycloalkylène, C6-C20-arylène ou hétéroarylène,
    où cycloalkylène et hétérocycloalkylène peuvent être interrompus par un ou plusieurs CO et/ou peuvent être substitués par un ou plusieurs radicaux RL2b identiques ou différents,
    où arylène et hétéroarylène peuvent être substitués par un ou plusieurs radicaux RL2c identiques ou différents, où
    RL2b est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11 ou phényle ;
    RL2c revêt l'une des significations indiquées pour RL2b ;
    L3 est choisi parmi C1-C30-alkylène, C2-C30-alcénylène, C3-C20-cycloalkylène, hétérocycloalkylène, C6-C20-arylène et hétéroarylène,
    où alkylène et alcénylène peuvent être interrompus par un ou plusieurs O, S, NR6 ou CO identiques ou différents et/ou peuvent porter un ou plusieurs radicaux RL3a identiques ou différents,
    où cycloalkylène et hétérocycloalkylène peuvent être interrompus par un ou plusieurs CO, et/ou peuvent être substitués par un ou plusieurs radicaux RL3b identiques ou différents,
    où arylène et hétéroarylène peuvent être substitués par un ou plusieurs radicaux RL3c identiques ou différents, où
    RL3a est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C10-cycloalkyle, hétérocyclyle, hétéroaryle, phényle et naphtyle, où les cinq radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R3aa identiques ou différents, où
    R3aa revêt l'une des significations indiquées pour RL2b ;
    RL3b revêt l'une des significations indiquées pour RL2b ;
    RL3c revêt l'une des significations indiquées pour RL2c ;
    L4 est choisi indépendamment les uns des autres parmi O, S, NR6, CO, C(O)O, OC(O), C(O)NR10, NR10C(O), C(S)NR12, NR12C(S), NR10SO2, C3-C20-cycloalkylène, hétérocycloalkylène, C6-C20-arylène, et hétéroarylène,
    où cycloalkylène et hétérocycloalkylène peuvent être interrompus par un ou plusieurs CO, et/ou peuvent être substitués par un ou plusieurs radicaux RL4b identiques ou différents,
    où arylène et hétéroarylène peuvent être substitués par un ou plusieurs radicaux RL4c identiques ou différents, où
    RL4b revêt l'une des significations indiquées pour RL2b ; et
    RL4c revêt l'une des significations indiquées pour RL2c ;
    RQa est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C10-cycloalkyle pouvant être interrompu par un ou deux groupements CO, hétérocyclyle pouvant être interrompu par un ou deux groupements CO, hétéroaryle, phényle et naphtyle, où les cinq radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux RQaa identiques ou différents, où
    RQaa est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9 et CONR10R11;
    RQb est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C1-C12-alkyle, C1-C12-halogénoalkyle, hétéroaryle, phényle et naphtyle, où les trois radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux RQba identiques ou différents, où RQba revêt l'une des significations indiquées pour RQaa ; RQc est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, phényle, C3-C10-cycloalkyle et hétérocyclyle, où dans les deux radicaux susmentionnés un ou deux groupements CH2 peuvent être remplacés par CO ;
    Q si b vaut 2, a vaut 0 et c vaut 0,
    est un bras de liaison divalent, qui est choisi parmi L5-C1-C30-alkylène-L5, L5-C2-C30-alcénylène-L5, L5-C3-C16-cycloalkylène-L5, L5-hétérocycloalkylène-L5, L5-C6-C20-arylène-L5, L5-hétéroaryléne-L5, L5-C1-C30-alkylène-L6-L5, L5-C2-C30-alcényléne-L6-L5, L5-C3-C16-cycloalkylène-L7-C3-C16-cycloalkylène-L5, L5-C3-C16-cycloalkylène-L7-hétérocycloalkylène-L5, L5-C3-C16-cycloalkylène-L7-C6-C20-arylène-L5, L5-C3-C16-cycloalkylène-L7-hétéroarylène-L5, L5-C6-C20-arylène-L7-C6-C20-arylène-L5, L5-C6-C20-arylène-L7-hétéroarylène-L5, L5-hétéroarylène-L7-hétéroarylène-L5, L5-C3-C16-cycloalkylène-L7-L8-L7-C3-C16-cycloalkylène-L5, L5-C3-C16-cycloalkylène-L7-L8-L7-hétérocycloalkylène-L5, L5-C3-C16-cycloalkylène-L7-L8-L7-C6-C20-arylène-L5, L5-C3-C16-cycloalkylène-L7-L8-L7-hétéroarylène-L5, L5-C6-C20-arylène-L7-L8-L7-C6-C20-arylène-L5, L5-C6-C20-arylène-L7-L8-L7-hétéroarylène-L5, L5-hétéroarylène-L7-L8-L7-hétéroarylène-L5,
    où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements L9 identiques ou différents, et/ou peuvent porter un ou plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arylène et chaque hétéroarylène peuvent porter un ou plusieurs radicaux RQc identiques ou différents, où
    L5 est indépendamment les uns des autres une liaison simple, S, O, NR6, CO, C(O)O, OC(O), NR10CO ou CONR10;
    L6 revêt l'une des significations indiquées pour L2 ;
    L7 revêt l'une des significations indiquées pour L1 ;
    L8 revêt l'une des significations indiquées pour L3 ;
    L9 revêt l'une des significations indiquées pour L4 ;
    ou
    Q si c vaut 2, a vaut 0 et b vaut 0,
    est un bras de liaison divalent qui est choisi parmi C1-C30-alkylène, C2-C30-alcénylène, C3-C16-cycloalkylène, hétérocycloalkylène, C6-C20-arylène, hétéroarylène, C1-C30-alkylène-L10, C2-C30-alcénylène-L10, C3-C16-cycloalkylène-L11-C3-C16-cycloalkylène, C3-C16-cycloalkylène-L11-hétérocycloalkylène, C3-C16-cycloalkylène-L11-C6-C20-arylène, C3-C16-cycloalkylène-L11-hétéroarylène, C6-C20-arylène-L11-C6-C20-arylène, C6-C20-arylène-L11-hétéroarylène, hétéroarylène-L11-hétéroarylène, C3-C16-cycloalkylène-L11-L12-L11-C3-C16-cycloalkylène, C3-C16-cycloalkylène-L11-L12-L11-C6-C20-arylène, C3-C16-cycloalkylène-L11-L12-L11-hétérocycloalkylène, C3-C6-cycloalkylène-L11-L12-L11-hétéroarylène, C6-C20-arylène-L11-L12-L11-C6-C20-arylène, C6-C20-arylène-L11-L12-L11-hétéroarylène, et hétéroarylène-L11-L12-L11-hétéroarylène,
    où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements L13 identiques ou différents, et/ou peuvent porter un ou plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arylène et chaque hétéroarylène peuvent porter un ou plusieurs radicaux RQc identiques ou différents, où
    L10 revêt l'une des significations indiquées pour L2 ;
    L11 revêt l'une des significations indiquées pour L1 ;
    L12 revêt l'une des significations indiquées pour L3 ;
    L13 revêt l'une des significations indiquées pour L4 ; ou
    Q si deux parmi les indices a, b ou c valent chacun 1 et l'indice restant vaut 0, la somme de a+b+c étant de 2,
    est un bras de liaison divalent, qui est choisi parmi C1-C30-alkylène, C2-C30-alcénylène, C3-C16-cycloalkylène, hétérocycloalkylène, C6-C20-arylène, hétéroarylène, C1-C30-alkylène-L10, C2-C30-alcénylène-L10, C3-C16-cycloalkylène-L11-C3-C16-cycloalkylène, C3-C16-cycloalkylène-L11-hétérocycloalkylène, C3-C16-cycloalkylène-L11-C6-C20-arylène, C3-C16-cycloalkylène-L11-hétéroarylène, C6-C20-arylène-L11-C6-C20-arylène, C6-C20-arylène-L11-hétéroarylène, hétéroarylène-L11-hétéroarylène, C3-C16-cycloalkylène-L11-L12-L11-C3-C16-cycloalkylène, C3-C16-cyclo-alkylèrie-L11-L12-L11-C6-C20-arylène, C3-C16-cycloalkylène-L11-L12-L11-hétérocycloalkylène, C3-C16-cycloalkylène-L11-L12-L11-hétéroarylène, C6-C20-arylène-L11-L12-L11-C6-C20-arylène, C6-C20-arylène-L11-L12-L11-hétéroarylène, et hètèroarylène-L11-L12-L11-hétéroarylène,
    où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements L13 identiques ou différents, et/ou peuvent porter un ou plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arylène et chaque hétéroarylène peuvent porter un ou plusieurs radicaux RQc identiques ou différents, où
    L10 revêt l'une des significations indiquées pour L2 ;
    L11 revêt l'une des significations indiquées pour L1 ;
    L12 revêt l'une des significations indiquées pour L3 ;
    L13 revêt l'une des significations indiquées pour L4 ; ou
    Q si la somme de a+b+c=3,
    est un bras de liaison trivalent, qui est choisi parmi C1-C30-alcanetriyle, C2-C30-alcènetriyle, C3-C16-cycloalcanetriyle, hétérocycloalcanetriyle, C6-C20-arènetriyle, hétéroarènetriyle, C1-C30-alcanetriyl-L14-L15, C2-C30-alcènetriyl-L14-L15, C1-C30-alkylène-L14-L16, C2-C30-alcènetriyl-L14-L15, C2-C30-alcénylène-L14-L16, C3-C16-cycloalcanetriyl-L14-L11-C3-C16-cycloalkylène, C3-C16-cycloalcanetriyl-L14-L15-C6-C20-arylène, C6-C20-arènetriyl-L14-L15-C6-C20-arylène, et C6-C20-arylène-L14-L15-C3-C16-cycloalcanetriyle,
    où chaque alcanetriyle, chaque alkylène, chaque alcènetriyle et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements L17 identiques ou différents et/ou peuvent porter un ou plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalcanetriyle, chaque cycloalkylène, chaque hétérocycloalcanetriyle et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arènetriyle, chaque arylène, chaque hétéroarènetriyle et chaque hétéroarylène peuvent porter un ou plusieurs radicaux RQc identiques ou différents, où
    L14 revêt l'une des significations indiquées pour L1 ;
    L15 revêt l'une des significations indiquées pour L2 ;
    L16 est C6-C20-arènetriyle, hétéroarènetriyle, C3-C20-cycloalcanetriyle ou hétérocycloalcanetriyle, où cycloalcanetriyle et hétérocycloalcanetriyle peuvent être interrompus par un ou plusieurs CO, et/ou peuvent être substitués par un ou plusieurs radicaux RL16b identiques ou différents ;
    où arènetriyle et hétéroarènetriyle peuvent être substitués par un ou plusieurs radicaux RL16c identiques ou différents, où
    RL16b revêt l'une des significations indiquées pour RL2b ; RL16c revêt l'une des significations indiquées pour RL2c ; L17 revêt l'une des significations indiquées pour L4 ;
    Q si la somme de a+b+c=4,
    est un bras de liaison tétravalent, qui est choisi parmi C1-C30-alcanetétrayle qui peut être interrompu par un ou plusieurs groupements L18 identiques ou différents et/ou peut porter un ou plusieurs radicaux RQa identiques ou différents ; où
    L18 revêt l'une des significations données pour L17 ;
    Q si la somme de a+b+c=6,
    est un bras de liaison hexavalent qui est choisi parmi C2-C30-alcanehexayle qui peut être interrompu par un ou plusieurs groupements L19 identiques ou différents et/ou peut porter un ou plusieurs radicaux RQa identiques ou différents ; où
    L19 revêt l'une des significations données pour L17 ;
    R1 est C1-C20-alkyle, C2-C20-alcényle, C2-C20-alcynyle, C3-C20-cycloalkyle, hétérocyclyle, C6-C20-aryle, hétéroaryle, C1-C20-alcanoyle, C3-C20-cycloalcanoyle, C2-C20-alcénoyle, C6-C20-aroyle, CSNR12R13, C(O)OR9 ou CSOR9,
    où C1-C20-alkyle, C2-C20-alcényle et C2-C20-alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO, et/ou peuvent porter un ou plusieurs radicaux R1a identiques ou différents,
    où C3-C20-cycloalkyle et hétérocyclyle peuvent être interrompus par un ou plusieurs groupements CO, et/ou peuvent porter un ou plusieurs radicaux R1b identiques ou différents,
    où C6-C20-aryle et hétéroaryle peuvent porter un ou plusieurs radicaux R1c identiques ou différents,
    où C1-C20-alcanoyle et C2-C20-alcénoyle peuvent porter un ou plusieurs radicaux R1a identiques ou différents,
    où C3-C20-cycloalcanoyle peut porter un ou plusieurs radicaux R1b identiques ou différents,
    où C6-C20-aroyle peut porter un ou plusieurs radicaux R1d identiques ou différents,
    où
    R1a est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C20-cycloalkyle qui peut être interrompu par un ou plusieurs groupements CO, hétérocyclyle qui peut être interrompu par un ou plusieurs groupements CO, hétéroaryle et C6-C10-aryle, où les quatre radicaux susmentionnés peuvent porter un ou plusieurs radicaux R1aa identiques ou différents, où
    R1aa est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-alkyle qui peut être interrompu par un ou plusieurs groupements choisis parmi CO, O, S, C(O)O, OC(O), C(O)S et SC(O), C1-C12-halogénoalkyle, C1-C12-hydroxyalkyle, C2-C12-alcényle, F, Cl, Br, I, NO2, SR4, OR5, NR6R7, COR8, COOR9 et CONR10R11 ;
    R1b est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C1-C12-alkyle, C1-C12-hydroxyalkyle, C1-C12-halogénoalkyle, C2-C12-alcényle, hétéroaryle et C6-C10-aryle, où les deux radicaux susmentionnés peuvent porter un ou plusieurs radicaux R1ba identiques ou différents, où
    R1ba revêt l'une des significations indiquées pour R1aa ;
    R1c est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, C1-C12-hydroxyalkyle, C2-C12-alcényle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, phényle, hétéroaryle, hétérocyclyle et C3-C10-cycloalkyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou deux groupements C=O et où phényle, hétéroaryle, hétérocyclyle et C3-C10-cycloalkyle peuvent porter un ou plusieurs radicaux R1ca identiques ou différents, où
    R1ca revêt l'une des significations indiquées pour R1aa ;
    R1d est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, C1-C12-hydroxyalkyle, C2-C12-alcényle, F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C20-cycloalkyle qui peut être interrompu par un ou plusieurs groupements CO, hétérocyclyle qui peut être interrompu par un ou plusieurs groupements CO, C6-C10-aryle et hétéroaryle, où les quatre radicaux susmentionnés peuvent porter un ou plusieurs radicaux R1da, où
    R1da revêt l'une des significations indiquées pour R1aa ; ou
    si b vaut 2, 3, 4 ou 6 et/ou c vaut 2, 3, 4 ou 6, deux radicaux R1 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes, ou
    si b vaut 2, 3, 4 ou 6, au moins un groupement -X-R1 peut être lié à un atome de carbone ou un atome d'azote de Q via un groupement de pontage divalent ayant de 1 à 10 atomes entre les liaisons flanquantes,
    R2 est hydrogène, SR4, OR5, NR1R14, COR8, SO2R4, COOR9, CONR10R11, SO2NR10R11, PO(OR9)2, CN, C1-C16-alkyle, C2-C20-alcényle, C2-C20-alcynyle, C3-C20-cycloalkyle, hétérocyclyle, C6-C20-aryle, hétéroaryle, C1-C20-alcanoyle, C2-C20-alcénoyle, C3-C20-cycloalcanoyle, C6-C20-aroyle ou un groupement E,
    où C1-C16-alkyle, C2-C20-alcényle et C2-C20-alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO, et/ou peuvent porter un ou plusieurs radicaux R2a identiques ou différents,
    où C3-C20-cycloalkyle et hétérocyclyle peuvent être interrompus par un ou plusieurs groupements CO, et/ou peuvent porter un ou plusieurs radicaux R2b identiques ou différents,
    où C6-C20-aryle et hétéroaryle peuvent porter un ou plusieurs radicaux R2c identiques ou différents,
    où C1-C20-alcanoyle et C2-C20-alcénoyle peuvent porter un ou plusieurs radicaux R2a identiques ou différents,
    où C3-C20-cycloalcanoyle peut porter un ou plusieurs radicaux R2b identiques ou différents,
    où C6-C20-aroyle peut porter un ou plusieurs radicaux R2d identiques ou différents, où
    R2a est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C20-cycloalkyle qui peut être interrompu par un ou plusieurs groupements CO, hétérocyclyle qui peut être interrompu par un ou plusieurs groupements CO, hétéroaryle et C6-C10-aryle, où les quatre radicaux susmentionnés peuvent porter un ou plusieurs radicaux R2aa identiques ou différents, où
    R2aa est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-alkyle qui peut être interrompu par un ou plusieurs groupements choisis parmi CO, O, S, C(O)O, OC(O), C(O)S et SC(O), C1-C12-halogénoalkyle, C1-C12-hydroxyalkyle, C2-C12-alcényle, phényle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9 et CONR10R11 ;
    R2b revêt l'une des significations indiquées pour R1b ;
    R2c revêt l'une des significations indiquées pour R1c ;
    R2d revêt l'une des significations indiquées pour R1d ;
    E est choisi parmi
    Figure imgb0333
    Figure imgb0334
    Figure imgb0335
     où
    # est le point de fixation au reste de la molécule ;
    d vaut 0, 1, 2, 3 ou 4 ;
    e vaut 0, 1, ou 2 ;
    f vaut 0, 1, ou 2 ;
    g vaut 0, 1, 2, 3 ou 4 ;
    R2e revêt l'une des significations indiquées pour R2c ;
    R2f est C1-C20-alkylène-COO-, C2-C20-alcénylène-COO-, C2-C20-alcynylène-COO-, C3-C20-cycloalkylène-COO-, hétérocycloalkylène-COO-, C6-C20-arylène-COO-, hétéroarylène-COO-, C1-C20-alkylène-S(O2)O-, C2-C20-alcénylène-S(O2)O-, C2-C20-alcynylène-S(O2)O-, C3-C20-cycloalkylène-S(O2)O-, hétérocycloalkylène-S(O2)O-, C6-C20-arylène-S(O2)O-, hétéroarylène-S(O2)O-, C1-C20-alkylène-OS(O2)O-, C2-C20-alcénylène-OS(O2)O-, C2-C20-alcynylène-OS(O2)O-, C3-C20-cycloalkylène-OS(O2)O-, hétérocycloalkylène-OS(O2)O-, C6-C20-arylène-OS(O2)O- ou hétéroarylène-OS(O2)O-,
    où chaque alkylène, chaque alcényle et chaque alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO, et/ou peuvent porter un ou plusieurs radicaux R2a identiques ou différents,
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou deux groupements CO et/ou peuvent porter un ou plusieurs radicaux R2b identiques ou différents,
    où chaque arylène et chaque hétéroarylène peuvent porter un ou plusieurs radicaux R2c,
    An- est Cl-, Br-, I-, SCN-, BF4 -, PF6 -, ClO4 -, SbF6 -, AsF6 -, C1-C20-alkyl-COO-, C1-C20-alkyl-S(O)2O-, C1-C20-alkyl-OS(O)2O-, C6-C20-aryl-COO-, C6-C20-aryl-S(O)2O- ou C6-C20-aryl-OS(O)2O-, où le motif aryle des trois radicaux susmentionnés peut être substitué par 1, 2, 3 ou 4 C1-C20-alkyle identiques ou différents ; ou
    -R2 conjointement avec -X-R1 peut être X-(C1-C20-alkylène)-Y, X-(C2-C20-alcénylène)-Y, X-(C3-C20-cycloalkylène)-Y, X-(hétérocycloalkylène)-Y, X-(o-phénylène)-Y, X-(o-xylylène)-Y, X-(o-phénylène-C1-C12-alkylène)-Y, X-(C1-C12-alkylène-o-phénylène)-Y, X-(O-C1-C20-alkylène)-Y, X-(S-C1-C20-alkylène)-Y ou X-(N(R6)-C1-C20alkylène)-Y, Y étant fixé à l'atome de carbone d'oxime portant X,
    où chaque alkylène et alcénylène peuvent comprendre un ou plusieurs groupements identiques ou différents choisis parmi O, S, NR6 et CO et/ou peuvent être substitués par un ou plusieurs radicaux R2g,
    où cycloalkylène et hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent éventuellement être substitués par un ou plusieurs radicaux R2h identiques ou différents,
    où chaque phénylène et le motif phénylène de o-xylylène peuvent être substitués par un ou plusieurs radicaux R2h identiques ou différents, où
    Y est O, S, NR14, CO, SC(O), OC(O), C(O)O, NR10C(O), C(O)NR10, NR10SO2 ou une liaison simple ;
    R2g est choisi indépendamment les uns des autres parmi F, Cl, Br, I, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, hétéroaryle et C6-C10-aryle où les deux radicaux susmentionnés peuvent porter un ou plusieurs radicaux R2ga, où
    R2ga est phénoxy ou revêt l'une des significations indiquées pour R1aa ;
    R2h est choisi indépendamment les uns des autres parmi F, Cl, Br, I, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C1-C12-alkyle, C1-C12-halogénoalkyle, hétéroaryle et C6-C10-aryle, où les deux radicaux susmentionnés peuvent porter un ou plusieurs radicaux R2ha, où R2ha revêt l'une des significations indiquées pour R1aa ;
    ou si X est S, -R2 est tel que défini ci-dessus ou -R2 conjointement avec -S-R1 est S-C(S)-NR12-C(O) ou S-C(=NOR15)-C(O)-NR12-C(O), où R15 est hydrogène ou phénylsulfonyle où le motif phényle peut être substitué par C1-C4-alkyle ou C1-C4-alcoxy ; ou
    si a vaut 2, 3, 4 ou 6 et/ou c vaut 2, 3, 4 ou 6, deux radicaux R2 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes ;
    R3 est C1-C20-alkyle, C2-C20-alcényle, C2-C20-alcynyle, C3-C20-cycloalkyle, hétérocyclyle, C6-C20-aryle ou hétéroaryle,
    où C1-C20-alkyle, C2-C20-alcényle et C2-C20-alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO, et/ou peuvent porter un ou plusieurs radicaux R3a identiques ou différents,
    où C3-C20-cycloalkyle et hétérocyclyle peuvent être interrompus par un ou plusieurs groupements CO, et/ou peuvent porter un ou plusieurs radicaux R3b identiques ou,
    où C6-C20-aryle et hétéroaryle peuvent porter un ou plusieurs identiques ou radicaux R3c, où
    R3a revêt l'une des significations indiquées pour R2a ;
    R3b revêt l'une des significations indiquées pour R1b ;
    R3c revêt l'une des significations indiquées pour R1c ; ou
    -X-R1 et R3 peuvent former ensemble un radical divalent choisi parmi X-(C1-C20-alkylène)-Z, X-(C2-C20-alcénylène)-Z, X-(C3-C20-cycloalkylène)-Z, X-(hétérocycloalkylène)-Z, X-(o-phénylène)-Z, X-(o-xylylène)-Z, X-(C0-C12-alkylène-hétéroarylène-C0-C12-alkylène)-Z; X-(o-phénylène-C1-C12-alkylène)-Z, X-(C1-C12-alkylène-o-phénylène) -Z et S-C(S)-NR12-C(O),
    où Z est fixé à l'atome de soufre du groupement sulfonate, où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi O, S, NR6 et CO, et/ou peuvent être substitués par un ou plusieurs radicaux R3g,
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent éventuellement être substitués par un ou plusieurs radicaux R3h identiques ou différents,
    où chaque phénylène et le motif phénylène de o-xylylène peuvent être substitués par un ou plusieurs radicaux R3h identiques ou différents, où
    R3g revêt l'une des significations indiquées pour R2g ;
    R3h revêt l'une des significations indiquées pour R2h ; et
    Z est O, S, NR14, CO, OC(O), SC(O), C(O)O, NR10C(O), C(O)NR10, NR10(SO2) ou une liaison simple ;
    R4 est choisi indépendamment les uns des autres parmi hydrogène, C1-C20-alkyle, C2-C12-alcényle,
    C3-C10-cycloalkyle, hétérocyclyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou plusieurs groupements C=O,
    C1-C20-alkyle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(C1-C8-alkyl)- et CO, et/ou peut porter un ou plusieurs radicaux R4a identiques ou différents,
    C2-C12-alcényle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, et -N(C1-C8-alkyl)-,
    -(CH2CH2O)mH, m valant 1-20,
    -(CH2CH2O)n(CO)-(C1-C8-alkyl), n valant 1-20,
    C2-C8-alcanoyle, C3-C6-alcénoyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, OH ou C1-C6-alcoxy,
    benzoyle qui peut être substitué par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, C1-C6-alkyle, OH et C1-C6-alcoxy,
    phényle et naphtyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R4c identiques ou différents,
    ou phényle ou naphtyle forment un cycle de 5 ou 6 chaînons avec le cycle phényle auquel SR4 est fixé via une liaison simple, C1-C4-alkylène, O, S, NR6 ou CO, où R4a est choisi indépendamment les uns des autres parmi F, Cl, Br, I, C3-C10-cycloalkyle, hétérocyclyle, phényle, OH, SH, CN, C3-C6-alcénoxy, OCH2CH2CN, OCH2CH2(CO)O(C1-C8-alkyl), O(CO)-(C1-C8-alkyl), O(CO)-phényle, (CO)OH et (CO)O(C1-C8-alkyl);
    R4c est choisi indépendamment les uns des autres parmi F, Cl, Br, I, C1-C12-alkyle, C1-C12-halogénoalkyle, C1-C12-alcoxy, phényl-C1-C3-alcoxy, phénoxy, C1-C12-alkylsulfanyle, phénylsulfanyle, -(CO)O(C1-C8-alkyl), (CO)N(C1-C8-alkyl)2 et phényle ;
    R5 est choisi indépendamment les uns des autres parmi hydrogène, C1-C20-alkyle, C2-C12-alcényle, C3-C10-cycloalkyle, hétérocyclyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou deux groupements C=O,
    C1-C20-alkyle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(C1-C8-alkyl)- et CO, et/ou peut porter un ou plusieurs radicaux R5a identiques ou différents, C2-C12-alcényle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, et -N(C1-C8-alkyl)-,
    -(CH2CH2O)mH, m valant 1-20,
    -(CH2CH2O)n(CO)-(C1-C8-alkyl), n valant 1-20, C2-C8-alcanoyle, C3-C6-alcénoyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, OH et C1-C6-alcoxy,
    C2-C8-alcanoyle, qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O- et -S- et peut être substitué par un ou plusieurs radicaux identiques ou différents choisis parmi hydroxyaminylène (=N-O), F, Cl, Br, I, OH et C1-C6-alcoxy,
    benzoyle qui peut être substitué par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, C1-C6-alkyle, OH et C1-C6-alcoxy,
    phényle et naphtyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R5c identiques ou différents,
    ou phényle ou naphtyle forment un cycle de 5 ou 6 chaînons avec le cycle phényle auquel OR5 est fixé via une liaison simple, C1-C4-alkylène, O, S, NR6 ou CO,
    où R5a revêt l'une des significations indiquées pour R4a ;
    R5c revêt l'une des significations indiquées pour R4c ;
    R6, R10 et R12 sont choisis indépendamment les uns des autres parmi hydrogène, OR5, C1-C20-alkyle, C2-C12-alcényle,
    C3-C10-cycloalkyle, hétérocyclyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou deux groupements C=O,
    C1-C20-alkyle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(C1-C8-alkyl)- et CO, et/ou peut porter un ou plusieurs radicaux R6a identiques ou différents,
    C2-C12-alcényle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, et -N(C1-C8-alkyl)-,
    -(CH2CH2O)oH, o valant 1-20,
    -(CH2CH2O)p(CO)-(C1-C8-alkyl), p valant 1-20, C2-C8-alcanoyle, C3-C6-alcénoyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, OH et C1-C6-alcoxy,
    benzoyle qui peut être substitué par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, C1-C6-alkyle, -OH et C1-C6-alcoxy,
    phényle et naphtyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R6c identiques ou différents, où
    R6a revêt l'une des significations indiquées pour R4a ;
    R6c revêt l'une des significations indiquées pour R4c ;
    ou
    deux radicaux R6 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes ; ou
    deux radicaux R10 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes ; ou
    deux radicaux R12 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes ;
    R7, R11 et R13 sont choisis indépendamment les uns des autres parmi OR5, C1-C20-alkyle, C2-C12-alcényle, C3-C10-cycloalkyle, hétérocyclyle, où dans les deux radicaux susmentionnés un ou deux groupements CH2 peuvent être remplacés par un groupement C=O,
    C1-C20-alkyle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(C1-C8-alkyl)- et CO, et/ou peut porter un ou plusieurs radicaux R7a identiques ou différents,
    C2-C12-alcényle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, et -N(C1-C8-alkyl)-,
    -(CH2CH2O)qH, q valant 1-20,
    -(CH2CH2O)r(CO)-(C1-C8-alkyl), r valant 1-20,
    C2-C8-alcanoyle, C3-C6-alcénoyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, OH et C1-C6-alcoxy,
    benzoyle qui peut être substitué par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, C1-C6-alkyle, OH et C1-C6-alcoxy,
    phényle et naphtyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R7c identiques ou différents, où
    R7a revêt l'une des significations indiquées pour R4a ;
    R7c revêt l'une des significations indiquées pour R4c ; ou
    R6 et R7, conjointement avec l'atome d'azote auquel ils sont fixés, forment un hétérocycle azoté de 5, 6 ou 7 chaînons saturé pouvant posséder un autre hétéroatome ou groupement hétéroatomique choisi dans le groupe constitué par CO, O, S et N(C1-C8-alkyl) comme chaînon et pouvant porter 1, 2, 3 ou 4 C1-C4-alkyle ; ou
    R10 et R11, conjointement avec l'atome d'azote auquel ils sont fixés, forment un hétérocycle azoté de 5, 6 ou 7 chaînons saturé pouvant posséder un autre hétéroatome ou groupement hétéroatomique choisi dans le groupe constitué par CO, O, S et N(C1-C8-alkyl) comme chaînon et pouvant porter 1, 2, 3 ou 4 C1-C4-alkyle ; ou
    R12 et R13, conjointement avec l'atome d'azote auquel ils sont fixés, forment un hétérocycle azoté de 5, 6 ou 7 chaînons saturé pouvant posséder un autre hétéroatome ou groupement hétéroatomique choisi dans le groupe constitué par CO, O, S et N(C1-C8-alkyl) comme chaînon et pouvant porter 1, 2, 3 ou 4 C1-C4-alkyle ;
    R8 est choisi indépendamment les uns des autres parmi hydrogène, C1-C20-alkyle, C2-C12-alcényle,
    C3-C10-cycloalkyle, hétérocyclyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou plusieurs groupements C=O,
    C1-C20-alkyle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(C1-C8-alkyl)- et CO, et/ou peut porter un ou plusieurs radicaux R8a identiques ou différents,
    C2-C12-alcényle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, et -N(C1-C8-alkyl)-,
    -(CH2CH2O)sH, s valant 1-20,
    -(CH2CH2O)t(CO)-(C1-C8-alkyl), t valant 1-20,
    C6-C20-aryle et hétéroaryle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R8c identiques ou différents, où
    R8a revêt l'une des significations indiquées pour R4a ;
    R8c revêt l'une des significations indiquées pour R4c ;
    R9 est choisi indépendamment les uns des autres parmi hydrogène, C1-C20-alkyle, C2-C12-alcényle, C3-C10-cycloalkyle, hétérocyclyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou plusieurs groupements C=O,
    C1-C20-alkyle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(C1-C8-alkyl)- et CO, et/ou peut porter un ou plusieurs radicaux R9a identiques ou différents,
    C2-C12-alcényle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, et -N(C1-C8-alkyl)-,
    -(CH2CH2O)uH, u valant 1-20,
    -(CH2CH2O)v(CO)-(C1-C8-alkyl), v valant 1-20,
    phényle et naphtyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R9c identiques ou différents, où
    R9a revêt l'une des significations indiquées pour R4a ;
    R9c revêt l'une des significations indiquées pour R4c ;
    R14 est C1-C20-alkyle, C2-C20-alcényle, C2-C20-alcynyle, C3-C20-cycloalkyle, hétérocyclyle, C6-C20-aryle, hétéroaryle, C1-C20-alcanoyle, C2-C20-alcénoyle, C3-C20-cycloalcanoyle, C6-C20-aroyle, CSNR12R13 ou CSOR9,
    où C1-C20-alkyle, C2-C20-alcényle et C2-C20-alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO et/ou peuvent porter un ou plusieurs radicaux R14a identiques ou différents,
    où C3-C20-cycloalkyle et hétérocyclyle peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux R14b identiques ou différents,
    où C6-C20-aryle, hétéroaryle peuvent porter un ou plusieurs identiques ou radicaux R14c,
    où C1-C20-alcanoyle, C2-C20-alcénoyle peuvent porter un ou plusieurs radicaux R14a identiques ou différents,
    où C3-C20-cycloalcanoyle peut porter un ou plusieurs radicaux R14b identiques ou différents,
    où C6-C20-aroyle peut porter un ou plusieurs radicaux R14d identiques ou différents, où
    R14a revêt l'une des significations indiquées pour R2a ;
    R14b revêt l'une des significations indiquées pour R1b ;
    R14c revêt l'une des significations indiquées pour R1c ;
    R14d revêt l'une des significations indiquées pour R1d ; ou
    R1 conjointement avec R14 peut être un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes ;
    ou deux radicaux R14 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes, et
    (b) au moins un composé polymérisable éthyléniquement insaturé.
  2. Composition selon la revendication 1, comprenant le composé de formule I où
    X est S ou NR14 ;
    Q si a vaut 1, b vaut 0 et c vaut 0,
    est un radical R1 ; ou
    Q si a vaut 2, b vaut 0 et c vaut 0
    est un bras de liaison divalent, qui est choisi parmi L-C1-C30-alkylène-L, L-C2-C30-alcénylène-L, L-C3-C16-cycloalkylène-L, L-hétérocycloalkylène-L, L-C6-C20-arylène-L, L-hétéroarylène-L, L-C1-C30-alkylène-L2-L, L-C2-C30-alcénylène-L2-L, L-C3-C16-cycloalkylène-L1-C3-C16-cycloalkylène-L, L-C3-C16-cycloalkylène-L1-hétérocycloalkylène-L, L-C3-C16-cycloalkylène-L1-C6-C20-arylène-L, L-C3-C16-cycloalkylène-L1-hétéroarylène-L, L-C6-C20-arylène-L1-C6-C20-arylène-L, L-C6-C20-arylène-L1-hétéroarylène-L, L-hétéroarylène-L1-hétéroarylène-L, L-C3-C16-cycloalkylène- L1- L3-L1-C3-C16-cycloalkylène- L, L-C3-C16-cycloalkylène-L1-L3-L1-hétérocycloalkylène-L, L-C3-C16-cycloalkylène-L1-L3-L1-C6-C20-arylène-L, L-C3-C16-cycloalkylène-L1-L3-L1-hétéroarylène-L, L-C6-C20-arylène-L1-L3-L1-C6-C20-arylène-L, L-C6-C20-arylène-L1-L3-L1-hétéroarylène-L, et L-hétéroarylène-L1-L3-L1-hétéroarylène-L,
    où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements non adjacents L4 identiques ou différents, et/ou peuvent porter un ou plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arylène et chaque hétéroarylène peuvent porter un ou plusieurs radicaux RQc identiques ou différents, où
    L est choisi indépendamment les uns des autres parmi une liaison simple, C(S)O, et C(S)NR12 ;
    L1 est indépendamment les uns des autres une liaison simple, O, S, NR14, CO, OC(O), C(O)O, C(S)O, OC(S), C(O)NR10, NR10C(O), C(S)NR12, NR12C(S) ou NR10SO2 ;
    L2 est C3-C20-cycloalkylène, hétérocycloalkylène, C6-C20-arylène ou hétéroarylène,
    où cycloalkylène et hétérocycloalkylène peuvent être interrompus par un ou plusieurs CO et/ou peuvent être substitués par un ou plusieurs radicaux RL2b identiques ou différents,
    où arylène et hétéroarylène peuvent être substitués par un ou plusieurs radicaux RL2c identiques ou différents,
    où
    RL2b est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11 ou phényle ;
    RL2c revêt l'une des significations indiquées pour RL2b ;
    L3 est choisi parmi C1-C30-alkylène, C2-C30-alcénylène, C3-C20-cycloalkylène, hétérocycloalkylène, C6-C20-arylène et hétéroarylène,
    où alkylène et alcénylène peuvent être interrompus par un ou plusieurs O, S, NR6 et CO identiques ou différents et/ou peuvent porter un ou plusieurs radicaux RL3a identiques ou différents,
    où cycloalkylène et hétérocycloalkylène peuvent être interrompus par un ou plusieurs CO, et/ou peuvent être substitués par un ou plusieurs radicaux RL3b identiques ou différents ;
    où arylène et hétéroarylène peuvent être substitués par un ou plusieurs radicaux RL3c identiques ou différents,
    où
    RL3a est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C10-cycloalkyle, hétérocyclyle, hétéroaryle, phényle et naphtyle, où les cinq radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R3aa identiques ou différents, où
    R3aa revêt l'une des significations indiquées pour RL2b ;
    RL3b revêt l'une des significations indiquées pour RL2b ;
    RL3c revêt l'une des significations indiquées pour RL2c ;
    L4 est choisi indépendamment les uns des autres parmi O, S, NR6, CO, C(O)O, OC(O), C(O)NR10, NR10C(O), C(S)NR12, NR12C(S), NR10SO2, C3-C20-cycloalkylène, hétérocycloalkylène, C6-C20-arylène, et hétéroarylène,
    où cycloalkylène et hétérocycloalkylène peuvent être interrompus par un ou plusieurs CO, et/ou peuvent être substitués par un ou plusieurs radicaux RL4b identiques ou différents,
    où arylène et hétéroarylène peuvent être substitués par un ou plusieurs radicaux RL4c identiques ou différents, où
    RL4b revêt l'une des significations indiquées pour RL2b ; et
    RL4c revêt l'une des significations indiquées pour RL2c ;
    RQa est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C10-cycloalkyle pouvant être interrompu par un ou deux groupements CO, hétérocyclyle pouvant être interrompu par un ou deux groupements CO, hétéroaryle, phényle et naphtyle, où les cinq radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux RQaa identiques ou différents, où
    RQaa est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9 et CONR10R11 ;
    RQb est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C1-C12-alkyle, C1-C12-halogénoalkyle, hétéroaryle, phényle et naphtyle, où les trois radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux RQba identiques ou différents, où
    RQba revêt l'une des significations indiquées pour RQaa ;
    RQc est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, phényle, C3-C10-cycloalkyle et hétérocyclyle, où dans les deux radicaux susmentionnés un ou deux groupements CH2 peuvent être remplacés par CO ;
    Q si b vaut 2, a vaut 0 et c vaut 0,
    est un bras de liaison divalent, qui est choisi parmi L5-C1-C30-alkylène-L5, L5-C2-C30-alcénylène-L5, L5-C3-C16-cycloalkylène-L5, L5-hétérocycloalkylène-L5, L5-C6-C20-arylène-L5, L5-hétéroarylène-L5, L5-C1-C30-alkylène-L6-L5, L5-C2-C30-alcénylène-L6-L5, L5-C3-C16-cycloalkylène-L7-C3-C16-cycloalkylène-L5, L5-C3-C16-cycloalkylène-L7-hétérocycloalkylène-L5, L5-C3-C16-cycloalkylène-L7-C6-C20-arylène-L5, L5-C3-C16-cycloalkylène-L7-hétéroarylène-L5, L5-C6-C20-arylène-L7-C6-C20-arylène-L5, L5-C6-C20-arylène-L7-hétéroarylène-L5, L5-hétéroarylène-L7-hétéroarylène-L5, L5-C3-C16-cycloalkylène-L7-L8-L7-C3-C16-cycloalkylène-L5, L5-C3-C16-cycloalkylène-L7-L8-L7-hétérocycloalkylène-L5, L5-C3-C16-cycloalkylène-L7-L8-L7-C6-C20-arylène-L5, L5-C3-C16-cycloalkylène-L7-L8-L7-hétéroarylène-L5, L5-C6-C20-arylène-L7-L8-L7-C6-C20-arylène-L5, L5-C6-C20-arylène-L7-L8-L7-hétéroarylène-L5, et L5-hétéroarylène-L7-L8-L7-hétéroarylène-L5,
    où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements L9 identiques ou différents, et/ou peuvent porter un ou plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arylène et hétéroarylène peuvent porter un ou
    plusieurs radicaux RQc identiques ou différents, où L5 est indépendamment les uns des autres une liaison simple, S, O, NR6, CO, C(O)O, OC(O), NR10CO ou CONR10 ;
    L6 revêt l'une des significations indiquées pour L2 ;
    L7 revêt l'une des significations indiquées pour L1 ;
    L8 revêt l'une des significations indiquées pour L3 ;
    L9 revêt l'une des significations indiquées pour L4 ;
    ou
    Q si c vaut 2, a vaut 0 et b vaut 0,
    est un bras de liaison divalent, qui est choisi parmi C1-C30-alkylène, C2-C30-alcénylène, C3-C16-cycloalkylène, hétérocycloalkylène, C6-C20-arylène, hétéroarylène, C1-C30-alkylène-L10, C2-C30-alcénylène-L10, C3-C16-cycloalkylène-L11-C3-C16-cycloalkylène, C3-C16-cycloalkylène-L11-hétérocycloalkylène, C3-C16-cycloalkylène-L11-C6-C20-arylène, C3-C16-cycloalkylène-L11-hétéroarylène, C6-C20-arylène-L11-C6-C20-arylène, C6-C20-arylène-L11-hétéroarylène, hétéroarylène-L11-hétéroarylène, C3-C16-cycloalkylène-L11-L12-L11-C3-C16-cycloalkylène, C3-C16-cycloalkylène-L11-L12-L11-C6-C20-arylène, C3-C16-cycloalkylène-L11-L12-L11-hétérocycloalkylène, C3-C16-cycloalkylène- L11-L12-L11-hétéroarylène, C6-C20-arylène-L11-L12-L11-C1-C2-arylène, C6-C20-arylène-L11-L12-L11-hétéroarylène,
    et hétéroarylène-L11-L12-L11-hétéroarylène,
    où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements L13 identiques ou différents, et/ou peuvent porter un ou
    plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arylène et chaque hétéroarylène peuvent porter un ou plusieurs radicaux RQc identiques ou différents, où
    L10 revêt l'une des significations indiquées pour L2 ;
    L11 revêt l'une des significations indiquées pour L1 ;
    L12 revêt l'une des significations indiquées pour L3 ;
    L13 revêt l'une des significations indiquées pour L4 ;
    ou
    Q si la somme de a+b+c=3,
    est un bras de liaison trivalent, qui est choisi parmi C1-C30-alcanetriyle, C2-C30-alcènetriyle, C3-C16-cycloalcanetriyle, hétérocycloalcanetriyle, C6-C20-arènetriyle, hétéroarènetriyle, C1-C30-alcanetriyl-L14-L15, C2-C30-alcènetriyl-L14-L15, C1-C30-alkylène-L14-L16, C2-C30-alcènetriyl-L14-L15, C2-C30-alcénylène-L14-L16, C3-C16-cycloalcanetriyl-L14-L11-C3-C16-cycloalkylène, C3-C16-cycloalcanetriyl-L14-L15-C6-C20-arylène, C6-C20-arènetriyl-L4-L15-C6-C20-arylène, et C6-C20-arylène-L14-L15-C3-C16-cycloalcanetriyle,
    où chaque alcanetriyle, chaque alkylène, chaque alcènetriyle et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements L17 identiques ou différents et/ou peuvent porter un ou plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalcanetriyle, chaque cycloalkylène,
    chaque hétérocycloalcanetriyle et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arènetriyle, chaque arylène, chaque hétéroarènetriyle et chaque hétéroarylène peuvent porter un ou plusieurs radicaux RQc identiques ou différents,
    où
    L14 revêt l'une des significations indiquées pour L1 ;
    L15 revêt l'une des significations indiquées pour L2 ;
    L16 est C6-C20-arènetriyle, hétéroarènetriyle, C3-C20-cycloalcanetriyle ou hétérocycloalcanetriyle, où cycloalcanetriyle et hétérocycloalcanetriyle peuvent être interrompus par un ou plusieurs CO, et/ou peuvent être substitués par un ou plusieurs radicaux RL16b identiques ou différents,
    où arènetriyle et hétéroarènetriyle peuvent être substitués par un ou plusieurs radicaux RL16c identiques ou différents, où
    RL16b revêt l'une des significations indiquées pour RL2b ;
    RL16c revêt l'une des significations indiquées pour RL2c ;
    L17 revêt l'une des significations indiquées pour L4 ;
    Q si la somme de a+b+c=4,
    est un bras de liaison tétravalent, qui est choisi parmi C1-C30-alcanetétrayle qui peut être interrompu par un ou plusieurs groupements L18 identiques ou différents et/ou peut porter un ou plusieurs radicaux RQa identiques ou différents ; où
    L18 revêt l'une des significations données pour L17 ;
    Q si la somme de a+b+c=6
    est un bras de liaison hexavalent qui est choisi parmi C2-C30-alcanehexayle qui peut être interrompu par un ou plusieurs groupements L19 identiques ou différents et/ou peut porter un ou plusieurs radicaux RQa identiques ou différents ; où
    L19 revêt l'une des significations données pour L17 ;
    R1 est C1-C20-alkyle, C2-C20-alcényle, C2-C20-alcynyle, C3-C20-cycloalkyle, hétérocyclyle, C6-C20-aryle, hétéroaryle, C1-C20-alcanoyle, C3-C20-cycloalcanoyle, C2-C20-alcénoyle, C6-C20-aroyle, CSNR12R13, C(O)OR9 ou CSOR9,
    où C1-C20-alkyle, C2-C20-alcényle et C2-C20-alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO, et/ou peuvent porter un ou plusieurs radicaux R1a identiques ou différents,
    où C3-C20-cycloalkyle et hétérocyclyle peuvent être interrompus par un ou plusieurs groupements CO, et/ou peuvent porter un ou plusieurs radicaux R1b identiques ou différents,
    où C6-C20-aryle et hétéroaryle peuvent porter un ou plusieurs radicaux R1c identiques ou différents,
    où C1-C20-alcanoyle et C2-C20-alcénoyle peuvent porter un ou plusieurs radicaux R1a identiques ou différents,
    où C3-C20-cycloalcanoyle peut porter un ou plusieurs radicaux R1b identiques ou différents,
    où C6-C20-aroyle peut porter un ou plusieurs radicaux R1d identiques ou différents, où
    R1a est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C20-cycloalkyle qui peut être interrompu par un ou plusieurs groupements CO, hétérocyclyle qui peut être interrompu par un ou plusieurs groupements CO, hétéroaryle et C6-C10-aryle, où les quatre radicaux susmentionnés peuvent porter un ou plusieurs radicaux R1aa identiques ou différents, où
    R1aa est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, C1-C12-hydroxyalkyle, C2-C12-alcényle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9 et CONR10R11 ;
    R1b est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C1-C12-alkyle, C1-C12-hydroxyalkyle, C1-C12-halogénoalkyle, C2-C12-alcényle, hétéroaryle et C6-C10-aryle, où les deux radicaux susmentionnés peuvent porter un ou plusieurs radicaux R1ba identiques ou différents, où
    R1ba revêt l'une des significations indiquées pour R1aa ;
    R1c est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, C1-C12-hydroxyalkyle, C2-C12-alcényle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, phényle, hétéroaryle, hétérocyclyle et C3-C10-cycloalkyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou deux groupements C=O et où phényle, hétéroaryle, hétérocyclyle et C3-C10-cycloalkyle peuvent porter un ou plusieurs radicaux R1ca identiques ou différents, où
    R1ca revêt l'une des significations indiquées pour R1aa ;
    R1d est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, C1-C12-hydroxyalkyle, C2-C12-alcényle, F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C20-cycloalkyle qui peut être interrompu par un ou plusieurs groupements CO, hétérocyclyle qui peut être interrompu par un ou plusieurs groupements CO, C6-C10-aryle et hétéroaryle, où les quatre radicaux susmentionnés peuvent porter un ou plusieurs radicaux R1da, où
    R1da revêt l'une des significations indiquées pour R1aa ; ou
    si b vaut 2, 3, 4 ou 6 et/ou c vaut 2, 3, 4 ou 6, deux radicaux R1 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes, ou
    si b vaut 2, 3, 4 ou 6, au moins un groupement -X-R1 peut être lié à un atome de carbone ou un atome d'azote de Q via un groupement de pontage divalent ayant de 1 à 10 atomes entre les liaisons flanquantes,
    R2 est hydrogène, SR4, OR5, NR1R14, COR8, SO2R4, COOR9, CONR10R11, SO2NR10R11, PO(OR9)2, CN, C1-C16-alkyle, C2-C20-alcényle, C2-C20-alcynyle, C3-C20-cycloalkyle, hétérocyclyle, C6-C20-aryle, hétéroaryle, C1-C20-alcanoyle, C2-C20-alcénoyle, C3-C20-cycloalcanoyle, C6-C20-aroyle ou un groupement E,
    où C1-C16-alkyle, C2-C20-alcényle et C2-C20-alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO, et/ou peuvent porter un ou plusieurs radicaux R2a identiques ou différents,
    où C3-C20-cycloalkyle et hétérocyclyle peuvent être interrompus par un ou plusieurs groupements CO, et/ou peuvent porter un ou plusieurs radicaux R2b identiques ou différents,
    où C6-C20-aryle et hétéroaryle peuvent porter un ou plusieurs radicaux R2c identiques ou différents,
    où C1-C20-alcanoyle et C2-C20-alcénoyle peuvent porter un ou plusieurs radicaux R2a identiques ou différents,
    où C3-C20-cycloalcanoyle peut porter un ou plusieurs radicaux R2b identiques ou différents,
    où C6-C20-aroyle peut porter un ou plusieurs radicaux R2d identiques ou différents, où
    R2a est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C20-cycloalkyle qui peut être interrompu par un ou plusieurs groupements CO, hétérocyclyle qui peut être interrompu par un ou plusieurs groupements CO, hétéroaryle et C6-C10-aryle, où les quatre radicaux susmentionnés peuvent porter un ou plusieurs radicaux R2aa identiques ou différents, où
    R2aa est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, C1-C12-hydroxyalkyle, C2-C12-alcényle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9 et CONR10R11 ;
    R2b revêt l'une des significations indiquées pour R1b ;
    R2c revêt l'une des significations indiquées pour R1c ;
    R2d revêt l'une des significations indiquées pour R1d ;
    E est choisi parmi
    Figure imgb0336
    Figure imgb0337
    Figure imgb0338
     où
    # est le point de fixation au reste de la molécule ;
    d vaut 0, 1, 2, 3 ou 4 ;
    e vaut 0, 1, ou 2 ;
    f vaut 0, 1, ou 2 ;
    g vaut 0, 1, 2, 3 ou 4 ;
    R2e revêt l'une des significations indiquées pour R2c ;
    R2f est C1-C20-alkylène-COO-, C2-C20-alcényléne-COO-, C2-C20-alcynylène-COO-, C3-C20-cycloalkylène-COO-, hétérocycloalkylène-COO-, C6-C20-arylène-COO-, hétéroarylène-COO-, C1-C20-alkylène-S(O2)O-, C2-C20-alcénylène-S (O2)O-, C2-C20-alcynylène-S(O2)O-, C3-C20-cycloalkylène-S (O2)O-, hétérocycloalkylène-S(O2)O-, C6-C20-arylène-S(O2)O-, hétéroarylène-S(O2)O-, C1-C20-alkylène-OS (O2)O-, C2-C20-alcénylène-OS(O2)O-, C2-C20-alcynylène-OS(O2)O-, C3-C20-cycloalkylène-OS(O2)O-, hétérocycloalkylène-OS(O2)O-, C6-C20-arylène-OS(O2)O- ou hétéroarylène-OS(O2)O-,
    où chaque alkylène, chaque alcényle et chaque alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO, et/ou peuvent porter un ou plusieurs radicaux R2a identiques ou différents,
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou deux groupements CO et/ou peuvent porter un ou plusieurs radicaux R2b identiques ou différents,
    où chaque arylène et chaque hétéroarylène peuvent porter un ou plusieurs radicaux R2c,
    An- est Cl-, Br-, I-, SCN-, BF4 -, PF6 -, ClO4 -, SbF6 -, AsF6 -, C1-C20-alkyl-COO-, C1-C20-alkyl-S(O)2O-, C1-C20-alkyl-OS(O)2O-, C6-C20-aryl-COO-, C6-C20-aryl-S(O)2O- ou C6-C20-aryl-OS(O)2O-, où le motif aryle des trois radicaux susmentionnés peut être substitué par 1, 2, 3 ou 4 C1-C20-alkyle identiques ou différents ; ou
    -R2 conjointement avec -X-R1 peut être X-(C1-C20-alkylène) -Y, X-(C2-C20-alcénylène)-Y, X-(C3-C20-cycloalkylène)-Y, X-(hétérocycloalkylène)-Y, X-(o-phénylène)-Y, X-(o-xylylène)-Y, X-(o-phénylène-C1-C12-alkylène)-Y, X-(C1-C12-alkylène-o-phénylène)-Y, X-(O-C1-C20-alkylène)-Y, X-(S-C1-C20-alkylène)-Y ou X-(N(R6)-C1-C20-alkylène)-Y, Y étant fixé à l'atome de carbone d'oxime portant X,
    où chaque alkylène et alcénylène peuvent comprendre un ou plusieurs groupements identiques ou différents choisis parmi O, S, NR6 et CO et/ou peuvent être substitués par un ou plusieurs radicaux R2g,
    où cycloalkylène et hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent éventuellement être substitués par un ou plusieurs radicaux R2h identiques ou différents,
    où chaque phénylène et le motif phénylène de o-xylylène peuvent être substitués par un ou plusieurs radicaux R2h identiques ou différents, où
    Y est O, S, NR14, CO, SC(O), OC(O), C(O)O, NR10C(O), C(O)NR10, NR10SO2 ou une liaison simple ;
    R2g est choisi indépendamment les uns des autres parmi F, Cl, Br, I, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, hétéroaryle et C6-C10-aryle où les deux radicaux susmentionnés peuvent porter un ou plusieurs radicaux R2ga, où
    R2ga revêt l'une des significations indiquées pour R1aa ;
    R2h est choisi indépendamment les uns des autres parmi F, Cl, Br, I, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C1-C12-alkyle, C1-C12-halogénoalkyle, hétéroaryle et C6-C10-aryle, où les deux radicaux susmentionnés peuvent porter un ou plusieurs radicaux R2ha, où
    R2ha revêt l'une des significations indiquées pour R1aa ;
    ou si X est S, -R2 est tel que défini ci-dessus ou -R2 conjointement avec -S-R1 est S-C(S)-NR12-C(O),
    ou si a vaut 2, 3, 4 ou 6 et/ou c vaut 2, 3, 4 ou 6, deux radicaux R2 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes ;
    R3 est C1-C20-alkyle, C2-C20-alcényle, C2-C20-alcynyle, C3-C20-cycloalkyle, hétérocyclyle, C6-C20-aryle ou hétéroaryle,
    où C1-C20-alkyle, C2-C20-alcényle et C2-C20-alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO, et/ou peuvent porter un ou plusieurs radicaux R3a identiques ou différents,
    où C3-C20-cycloalkyle et hétérocyclyle peuvent être interrompus par un ou plusieurs groupements CO, et/ou peuvent porter un ou plusieurs radicaux R3b identiques ou différents,
    où C6-C20-aryle et hétéroaryle peuvent porter un ou plusieurs identiques ou radicaux R3c, où
    R3a revêt l'une des significations indiquées pour R2a ;
    R3b revêt l'une des significations indiquées pour R1b ;
    R3c revêt l'une des significations indiquées pour R1c ; ou
    -X-R1 et R3 peuvent former ensemble un radical divalent choisi parmi X-(C1-C20-alkylène)-Z, X-(C2-C20-alcénylène)-Z, X-(C3-C20-cycloalkylène)-Z, X-(hétérocycloalkylène)-Z, X-(o-phénylène)-Z, X-(o-xylylène)-Z, X-(C0-C12-alkylène-hétéroarylène-C0-C12-alkylène)-Z ; X-(o-phénylène-C1-C12-alkylène)-Z, X-(C1-C12-alkylène-o-phénylène)-Z et S-C(S)-NR12-C(O),
    où Z est fixé à l'atome de soufre du groupement sulfonate, où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi O, S, NR6 et CO et/ou peuvent être substitués par un ou plusieurs radicaux R3g,
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent éventuellement être substitués par un ou plusieurs radicaux R3h identiques ou différents,
    où chaque phénylène et le motif phénylène de o-xylylène peuvent être substitués par un ou plusieurs radicaux R3h identiques ou différents, où
    R3g revêt l'une des significations indiquées pour R2g ;
    R3h revêt l'une des significations indiquées pour R2h ;
    et Z est O,S, NR14, CO, OC(O), SC(O), C(O)O, NR10C(O), C(O)NR10, NR10(SO2) ou une liaison simple ;
    R5 est choisi indépendamment les uns des autres parmi hydrogène, C1-C20-alkyle, C2-C12-alcényle, C3-C10-cycloalkyle, hétérocyclyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou deux groupements C=O,
    C1-C20-alkyle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(C1-C8-alkyl)- et CO, et/ou peut porter un ou plusieurs radicaux R5a identiques ou différents, C2-C12-alcényle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, et -N(C1-C8-alkyl)-,
    -(CH2CH2O)mH, m valant 1-20,
    -(CH2CH2O)n(CO)-(C1-C8-alkyl), n valant 1-20,
    C2-C8-alcanoyle, C3-C6-alcénoyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, OH et C1-C6-alcoxy,
    benzoyle qui peut être substitué par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, C1-C6-alkyle, OH et C1-C6-alcoxy,
    phényle et naphtyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R5c identiques ou différents,
    ou phényle ou naphtyle forment un cycle de 5 ou 6 chaînons avec le cycle phényle auquel OR5 est fixé via une liaison simple, C1-C4-alkylène, O, S, NR6 ou CO, où
    R5a revêt l'une des significations indiquées pour R4a ;
    R5c revêt l'une des significations indiquées pour R4c.
  3. Composition selon l'une quelconque des revendications précédentes, où le composé de formule I est choisi parmi les composés de formules IA.1, IA, IB et IC
    Figure imgb0339
    Figure imgb0340
     où
    Q, X, R1 R2 et R3 sont tels que définis selon la revendication 1 ou 2 ;
    a vaut 2, 3 ou 4 ;
    b vaut 2 ou 3 ; et
    c vaut 2 ou 3.
  4. Composition selon la revendication 3, comprenant le composé de formule IA.1, où
    R3 est C2-C4-alkyle, C2-C6-alcényle, hétérocyclyle de 5 ou 6 chaînons saturé comprenant, outre des atomes de carbone, 1 ou 2 hétéroatomes ou groupements hétéroatomiques choisis parmi O, S, SO et SO2, thiényle, phényle ou benzyle où chacun parmi les deux radicaux susmentionnés peut être non substitué ou peut porter un, deux, trois, quatre ou cinq radicaux choisis indépendamment les uns des autres parmi fluor, nitro, C1-C4-alkyle, C1-C4-alcoxy, C1-C4-fluoroalkyle, C1-C4-alcoxycarbonyle et C2-C6-alcényle ; et
    -X-R1 conjointement avec R2 est -X-(C1-C8-alkylène)-OC(O)- ou -X-(o-phénylène)-O-C(O)- et X est N(C1-C8-alkyl), N(benzyl), N(C1-C4-alcoxy-C1-C4-alkyl) ou S.
  5. Composition selon la revendication 3, comprenant le composé de formule IA.1, où
    X est S, N(C1-C6-alkyl), N(C1-C4-alcoxy-C1-C4-alkyl), N(benzyl), N(phénéthyl), N(C2-C6-alcényl) ou N(C3-C8-cycloalkyl-C1-C4-alkyl) ;
    R1 est C3-C6-alkyle, mercapto-C3-C6-alkyle, mercapto-C3-C6-alkyl-S-C1-C2-alkyle, C2-C4-alcényle, C3-C8-cycloalkyl-C1-C4-alkyle, C1-C4-alcoxy-C1-C4-alcoxycarbonyl-C1-C2-alkyle, C1-C4-alcoxycarbonyl-C1-C2-alkyle, C1-C4-halogénoalcoxycarbonyl-C1-C2-alkyle, benzylsulfanyl-C1-C4-alkyl-O-C1-C4-alkyle, phénéthylsulfanyl-C1-C4-alkyl-OC1-C4-alkyle, C1-C8-cycloalkyle, benzyle qui est substitué par C1-C4-alcanoyl-S-C1-C2-alkyle, phényle ou benzyle où phényle et le motif phényle du benzyle peuvent être substitués par un, deux ou trois radicaux choisis parmi nitro et C1-C4-alkyle ; ou
    R1 et R14, conjointement avec l'atome d'azote auquel ils sont liés, forment un hétérocycle de 5, 6 ou 7 chaînons saturé ou insaturé pouvant comporter un autre hétéroatome choisi parmi O, S et N comme chaînon ;
    R2 est C1-C6-alkyle, C3-C8-cycloalkyle, C1-C4-alcoxy-carbonyle, C1-C4-halogénoalcoxycarbonyle, morpholinoamide, -COO(CH2CH2O)v(C1-C4-alkyl), v valant 1, 2, 3 ou 4,
    pyridyle, phényle pouvant être substitué par 1, 2 ou 3 radicaux choisis parmi nitro, C1-C4-alkyle, C1-C4-alcoxycarbonyle ou
    Figure imgb0341
     R2f étant C1-C12-alkylène-COO-, C1-C12-alkylène-S(O)2O- ou C1-C12-alkylène-OS(O)2O ; et
    R3 est C1-C4-alkyle, C2-C6-alcényle, hétérocyclyle de 5 ou 6 chaînons saturé comprenant, outre des atomes de carbone, 1 ou 2 hétéroatomes ou groupements hétéroatomiques choisis parmi O, S, SO et SO2, thiényle, phényle ou benzyle où chacun parmi les deux radicaux susmentionnés peut être non substitué ou peut porter un, deux, trois, quatre ou cinq radicaux choisis indépendamment les uns des autres parmi fluor, nitro, C1-C4-alkyle, C1-C4-alcoxy, C1-C4-fluoroalkyle, C1-C4-alcoxycarbonyle et C2-C6-alcényle.
  6. Composition selon la revendication 3, comprenant le composé de formule IA, où
    a vaut 2,
    X est S, N(C1-C6-alkyl), N(C1-C4-alcoxy-C1-C4-alkyl), N(benzyl), N(phénéthyl), N(C2-C6-alcényl) ou N(C3-C8-cycloalkyl-C1-C4-alkyl) ;
    chaque R2 est choisi indépendamment dans le groupe constitué par C1-C4-alkyle, C1-C4-alcoxycarbonyle et morpholinoamide ;
    chaque R3 est choisi indépendamment dans le groupe constitué par C1-C4-alkyle, C2-C6-alcényle, hétérocyclyle de 5 ou 6 chaînons saturé comprenant, outre des atomes de carbone, 1 ou 2 hétéroatomes ou groupements hétéroatomiques choisis parmi O, S, SO et SO2, thiényle, phényle ou benzyle où chacun parmi les deux radicaux susmentionnés peut être non substitué ou peut porter un, deux, trois, quatre ou cinq radicaux choisis indépendamment les uns des autres parmi fluor, nitro, C1-C4-alkyle, C1-C4-alcoxy, C1-C4-fluoroalkyle, C1-C4-alcoxycarbonyle et C2-C6-alcényle ;
    Q est phénylène, phénylène-S-phénylène, ou C1-C10-alkylène qui peut être interrompu par un, deux, trois ou quatre groupements non adjacents choisis parmi phénylène, O et S.
  7. Composition selon la revendication 3, comprenant le composé de formule IA, où
    a vaut 3 ;
    X est S ;
    chaque R2 est choisi indépendamment dans le groupe constitué par C1-C4-alkyle, C1-C4-alcoxycarbonyle et morpholinoamide ;
    chaque R3 est choisi indépendamment dans le groupe constitué par C1-C4-alkyle, C2-C6-alcényle, hétérocyclyle de 5 ou 6 chaînons saturé comprenant, outre des atomes de carbone, 1 ou 2 hétéroatomes ou groupements hétéroatomiques choisis parmi O, S, SO et SO2, thiényle, phényle ou benzyle où chacun parmi les deux radicaux susmentionnés peut être non substitué ou peut porter un, deux, trois, quatre ou cinq radicaux choisis indépendamment les uns des autres parmi fluor, nitro, C1-C4-alkyle, C1-C4-alcoxy, C1-C4-fluoroalkyle, C1-C4-alcoxycarbonyle et C2-C6-alcényle ;
    Q est C1-C20-alcanetriyle, qui peut être interrompu par 3, 4, 5, 6, 7, 8, ou 9 groupements identiques ou différents choisis parmi O, S, NR6, CO, C(O)O.
  8. Composition selon la revendication 3, comprenant le composé de formule IA, où
    a vaut 4 ;
    X est S ;
    chaque R2 est choisi indépendamment dans le groupe constitué par C1-C4-alkyle ou C1-C4-alcoxycarbonyle ;
    chaque R3 est choisi indépendamment dans le groupe constitué par C1-C4-alkyle, C2-C6-alcényle, hétérocyclyle de 5 ou 6 chaînons saturé comprenant, outre des atomes de carbone, 1 ou 2 hétéroatomes ou groupements hétéroatomiques choisis parmi O, S, SO et SO2, thiényle, phényle ou benzyle où chacun parmi les deux radicaux susmentionnés peut être non substitué ou peut porter un, deux, trois, quatre ou cinq radicaux choisis indépendamment les uns des autres parmi fluor, nitro, C1-C4-alkyle, C1-C4-alcoxy, C1-C4-fluoroalkyle, C1-C4-alcoxycarbonyle et C2-C6-alcényle ;
    Q est C1-C20-alcanetétrayle, qui peut être interrompu par 3, 4, 5, 6, 7, 8, ou 9 groupements identiques ou différents choisis parmi O, S, NR6, CO et C(O)O.
  9. Composition selon la revendication 3, comprenant le composé de formule IB, où
    b vaut 2 ;
    X est S ;
    chaque R1 est choisi indépendamment dans le groupe constitué par C1-C6-alkyle, mercapto-C3-C6-alkyle, mercapto-C3-C6-alkyl-S-C1-C2-alkyle, C2-C4-alcényle, benzyle, C1-C4-alcoxycarbonyl-C1-C4-alkyle ; phényle ; et phényle qui est substitué par un ou deux C1-C4-alkyle ou C2-C4-alcényle ; et
    Q est C1-C10-alkylène qui peut être interrompu par un, deux, trois ou quatre autres atomes non adjacents choisis parmi O et S.
  10. Composition selon la revendication 3, comprenant le composé de formule IC, où
    c vaut 2 ;
    X est S ;
    chaque R1 est choisi indépendamment dans le groupe constitué par C1-C6-alkyle, C3-C8-alcényle, mercapto-C3-C6-alkyle, mercapto-C3-C6-alkyl-S-C1-C2-alkyle, C1-C4-alcoxy-C1-C4-alcoxycarbonyl-C1-C2-alkyle, C1-C4-alcoxy-carbonyl-C1-C2-alkyle, C2-C4-alcényle, C3-C3-cycloalkyle, C3-C8-cycloalkyl-C1-C2-alkyle, phényl-C1-C4-alkyl-sulfanyl-C1-C4-alkyl-O-C1-C4-alkyle, phénéthylsulfanyl-C1-C4-alkyl-O-C1-C2-alkyle, phényle, phénéthyle et benzyle où chaque motif phényle dans les cinq radicaux susmentionnés peut être substitué par un, deux ou trois radicaux choisis parmi nitro, C2-C4-alcényle et C1-C4-alkyle ;
    chaque R2 est choisi indépendamment dans le groupe constitué par C1-C6-alkyle, C1-C4-alcoxycarbonyle, morpholinoamide et C1-C4-alcoxy-C1-C4-alcoxy-C1-C4-alcoxycarbonyle ; et
    Q est C1-C10-alkylène qui peut être interrompu par un, deux, trois ou quatre groupements non adjacents choisis parmi O, S, phénylène et naphtylène.
  11. Composition selon la revendication 1 ou 2, comprenant le composé de formule I choisi parmi les composés de formule ID,
    Figure imgb0342
     où
    Q est un bras de liaison divalent, choisi parmi phénylène, phénylène-S-phénylène, ou C1-C10-alkylène qui peut être interrompu par un, deux, trois ou quatre groupements non adjacents choisis parmi phénylène, O et S ;
    chaque X est S ;
    R1 est C3-C6-alkyle, mercapto-C3-C6-alkyle, mercapto-C3-C6-alkyl-S-C1-C2-alkyle, C2-C4-alcényle, C3-C8-cycloalkyl-C1-C4-alkyle, C1-C4-alcoxy-C1-C4-alcoxycarbonyl-C1-C2-alkyle, C1-C4-alcoxycarbonyl-C1-C2-alkyle, benzyl-sulfanyl-C1-C4-alkyl-O-C1-C4-alkyle, phénéthylsulfanyl-C1-C4-alkyl-O-C1-C4-alkyle, phényle ou benzyle où phényle et le motif phényle du benzyle peuvent être substitués par un, deux ou trois radicaux choisis parmi nitro et C1-C4-alkyle, benzyle qui est substitué par C1-C4-alcanoyl-S-C1-C2-alkyle ;
    chaque R2 est indépendamment les uns des autres choisi parmi indépendamment choisi dans le groupe constitué par C1-C6-alkyle, C1-C4-alcoxycarbonyle, morpholinoamide et C1-C4-alcoxy-C1-C4-alcoxy-C1-C4-alcoxycarbonyle ; et
    R3 est C1-C4-alkyle, C2-C6-alcényle, hétérocyclyle de 5 ou 6 chaînons saturé comprenant, outre des atomes de carbone, 1 ou 2 hétéroatomes ou groupements hétéroatomiques choisis parmi O, S, SO et SO2, thiényle, phényle ou benzyle où chacun parmi les deux radicaux susmentionnés peut être non substitué ou peut porter un, deux, trois, quatre ou cinq radicaux choisis indépendamment les uns des autres parmi fluor, nitro, C1-C4-alkyle, C1-C4-alcoxy, C1-C4-fluoroalkyle, C1-C4-alcoxycarbonyle et C2-C6-alcényle.
  12. Composition selon l'une quelconque des revendications précédentes, où le au moins un composé polymérisable éthyléniquement insaturé est un monomère d'acrylate.
  13. Composition selon l'une quelconque des revendications précédentes composition selon l'une quelconque des revendications 1 à 12, comprenant en outre au moins un photo-initiateur (c).
  14. Méthode de préparation d'un matériau polymère, comprenant les étapes consistant à :
    i) fournir une composition comprenant au moins un composé polymérisable éthyléniquement insaturé et au moins un composé de sulfonate d'oxime de formule I telle que définie selon l'une quelconque des revendications 1 à 13, et
    ii) soumettre la composition aux conditions de réaction d'une polymérisation radicalaire.
  15. Utilisation d'une composition selon les revendications 1 à 13, pour la production de filtres colorés pour des applications d'affichage, d'espaceurs pour LCD, de couche de finition pour filtre coloré et LCD, de matériau d'étanchéité pour LCD, de films optiques pour diverses applications d'affichage, d'adhésif conducteur anisotropique pour LCD, de couche isolante pour LCD, afin de générer des structures ou des couches dans les procédés de fabrication d'écrans à plasma, d'écrans électroluminescents et de LCD, afin de fabriquer des épargnes de soudage, des couches diélectriques dans une couche de renforcement séquentiel d'un circuit imprimé nu.
  16. Composé de sulfonate d'oxime de formule I,

            QAaBbCc     (I)

    où a vaut 0, 1, 2, 3, 4 ou 6 ;
    b vaut 0, 1, 2, 3, 4 ou 6 ; et
    c vaut 0, 1, 2, 3, 4 ou 6 ;
    où la somme de a+b+c vaut 1, 2, 3, 4 ou 6
    où A est un groupement
    Figure imgb0343
    B est un groupement
    Figure imgb0344
    C est un groupement
    Figure imgb0345
     où # désigne le point de fixation à Q ;
    X est S, SO2 ou NR14 ;
    Q si a vaut 1, b vaut 0 et c vaut 0,
    est un radical R1 ; ou
    Q si a vaut 2, b vaut 0 et c vaut 0
    est un bras de liaison divalent qui est choisi parmi L-C1-C30-alkylène-L, L-C2-C30-alcénylène-L, L-C3-C16-cycloalkylène-L, L-hétérocycloalkylène-L, L-C6-C20-arylène-L, L-hétéroarylène-L, L-C1-C30-alkylène-L2-L, L-C2-C30-alcénylène-L2-L, L-C3-C16-cycloalkylène-L1-C3-C16-cycloalkylène-L, L-C3-C,6-cycloalkylène-L1-hétérocycloalkylène-L, L-C3-C16-cycloalkylène-L1-C6-C20-arylène-L, L-C3-C16-cycloalkylène-L1-hétéroarylène-L, L-C6-C20-arylène-L-C6-C20-arylène-L, L-C6-C20-arylène-L1-hétéroarylène-L, L-hétéroarylène-L1-hétéroarylène-L, L-C3-C16-cycloalkylène-L1-L3-L1-C3-C16-cycloalkylène-L, L-C3-C16-cycloalkylène-L1-L3-L1-hétérocycloalkylène-L, L-C3-C16-cycloalkylène-L1-L3-L1-C6-C20-arylène-L, L-C3-C16-cycloalkylène-L1-L3-L1-hétéroarylène-L, L-C6-C20-arylène-L1-L3-L1-C6-C20-arylène-L, L-C6-C20-arylène-L1-L3-L1-hétéroarylène-L, et L-hétéroarylène-L1-L3-L1-hétéroarylène-L,
    où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements L4 non adjacents identiques ou différents, et/ou peuvent porter un ou plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arylène et chaque hétéroarylène peuvent porter un ou plusieurs radicaux RQc identiques ou différents,
    où
    L est choisi indépendamment les uns des autres parmi une liaison simple, C(S)O, C(S)NR12 ;
    L1 est indépendamment les uns des autres une liaison simple, O, S, NR14, CO, OC(O), C(O)O, C(S)O, OC(S), C(O)NR10, NR10C(O), C(S)NR12, NR12C(S) et NR10SO2 ;
    L2 est C3C20-cycloalkylène, hétérocycloalkylène, C6-C20-arylène ou hétéroarylène,
    où cycloalkylène et hétérocycloalkylène peuvent être interrompus par un ou plusieurs CO et/ou peuvent être substitués par un ou plusieurs radicaux RL2b identiques ou différents,
    où arylène et hétéroarylène peuvent être substitués par un ou plusieurs radicaux RL2c identiques ou différents, où
    RL2b est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11 ou phényle ;
    RL2c revêt l'une des significations indiquées pour RL2b ;
    L3 est choisi parmi C1-C30-alkylène, C2-C30-alcénylène, C3-C20-cycloalkylène, hétérocycloalkylène, C6-C20-arylène et hétéroarylène,
    où alkylène et alcénylène peuvent être interrompus par un ou plusieurs O,S, NR6 ou CO identiques ou différents et/ou peuvent porter un ou plusieurs radicaux RL3a identiques ou différents,
    où cycloalkylène et hétérocycloalkylène peuvent être interrompus par un ou plusieurs CO, et/ou peuvent être substitués par un ou plusieurs radicaux RL3b identiques ou différents,
    où arylène et hétéroarylène peuvent être substitués par un ou plusieurs radicaux RL3c identiques ou différents, où
    RL3a est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C10-cycloalkyle, hétérocyclyle, hétéroaryle, phényle et naphtyle, où les cinq radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R3aa identiques ou différents, où
    R3aa revêt l'une des significations indiquées pour RL2b ;
    RL3b revêt l'une des significations indiquées pour RL2b ;
    RL3c revêt l'une des significations indiquées pour RL2c ;
    L4 est choisi indépendamment les uns des autres parmi O, S, NR6, CO, C(O)O, OC(O), C(O)NR10, NR10C(O), C(S)NR12, NR12C (S) , NR10SO2, C3-C20-cycloalkylène, hétérocycloalkylène, C6-C20-arylène, et hétéroarylène,
    où cycloalkylène et hétérocycloalkylène peuvent être interrompus par un ou plusieurs CO, et/ou peuvent être substitués par un ou plusieurs radicaux RL4b identiques ou différents,
    où arylène et hétéroarylène peuvent être substitués par un ou plusieurs radicaux RL4c identiques ou différents, où
    RL4b revêt l'une des significations indiquées pour RL2b ; et
    RL4c revêt l'une des significations indiquées pour RL2c ;
    RQa est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C10-cycloalkyle pouvant être interrompu par un ou deux groupements CO, hétérocyclyle pouvant être interrompu par un ou deux groupements CO, hétéroaryle, phényle et naphtyle, où les cinq radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux RQaa identiques ou différents, où
    RQaa est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9 et CONR10R11 ;
    RQb est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C1-C12-alkyle, C1-C12-halogénoalkyle, hétéroaryle, phényle et naphtyle, où les trois radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux RQba identiques ou différents, où RQba revêt l'une des significations indiquées pour RQaa ;
    RQc est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11,phényle, C3-C10-cycloalkyle et hétérocyclyle, où dans les deux radicaux susmentionnés un ou deux groupements CH2 peuvent être remplacés par CO ;
    Q si b vaut 2, a vaut 0 et c vaut 0,
    est un bras de liaison divalent, qui est choisi parmi L5-C1-C30-alkylène-L5, L5-C2-C30-alcénylène-L5, L5-C3-C16-cycloalkylène-L5, L5-hétérocycloalkylène-L5, L5-C6-C20-arylène-L5, L5-hétéroaryléne-L5, L5-C1-C30-alkylène-L6-L5, L5-C2-C30-alcénylène-L6-L5, L5-C3-C16-cycloalkylène-L7-C3-C16-cycloalkylène-L5, L5-C3-C16-cycloalkylène-L7-hétérocycloalkyléne-L5, L5-C3-C16-cycloalkylène-L7-C6-C20-arylène-L5, L5-C3-C16-cycloalkylène-L7-hétéroarylène-L5, L5-C6-C20-arylène-L7-C6-C20-arylène-L5, L5-C6-C20-arylène-L7-hétéroarylène-L5, L5-hétéroarylène-L7-hétéroarylène-L5, L5-C3-C16-cycloalkylène-L7-L8-L7-C3-C16-cycloalkylène-L5, L5-C3-C16-cycloalkylène-L7-L8-L7-hétérocycloalkylène-L5, L5-C3-C16-cycloalkylène-L7-L8-L7-C6-C20-arylène-L5, L5-C3-C16-cycloalkylène-L7-L8-L7-hétéroarylène-L5, L5-C6-C20-arylène-L7-L8-L7-C6-C20-arylène-L5, L5-C6-C20-arylène-L7-L8-L7-hétéroarylène-L5, L5-hétéroarylène-L7-L8-L7-hétéroarylène-L5,
    où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements L9 identiques ou différents, et/ou peuvent porter un ou plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arylène et chaque hétéroarylène peuvent porter un ou plusieurs radicaux RQc identiques ou différents, où
    L5 est indépendamment les uns des autres une liaison simple, S, O, NR6, CO, C(O)O, OC(O), NR10CO ou CONR10 ;
    L6 revêt l'une des significations indiquées pour L2 ;
    L7 revêt l'une des significations indiquées pour L1 ;
    L8 revêt l'une des significations indiquées pour L3 ;
    L9 revêt l'une des significations indiquées pour L4 ;
    ou
    Q si c vaut 2, a vaut 0 et b vaut 0,
    est un bras de liaison divalent qui est choisi parmi C1-C30-alkylène, C2-C30-alcénylène, C3-C16-cycloalkylène, hétérocycloalkylène, C6-C20-arylène, hétéroarylène, C1-C30-alkylène-L10, C2-C30-alcénylène-L10, C3-C16-cycloalkylène-L11-C3-C16-cycloalkylène, C3-C16-cycloalkylène-L11-hétérocycloalkylène, C3-C16-cycloalkylène-L11-C6-C20-arylène, C3-C16-cycloalkylène-L11-hétéroarylène, C6-C20-arylène-L11-C6-C20-arylène, C6-C20-arylène-L11-hétéroarylène, hétéroarylène-L11-hétéroarylène, C3-C16-cycloalkylène-L11-L12-L11-C3-C16-cycloalkylène, C3-C16-cycloalkylène-L11-L12-L11-C6-C20-arylène, C3-C16-cycloalkylène-L11-L12-L11-hétérocycloalkylène, C3-C6-cycloalkylène-L11-L12-L11-hétéroarylène, C6-C20-arylène-L11-L12-L11-C6-C20-arylène, C6-C20-arylène-L11-L12-L11-hétéroarylène, et hétéroarylène-L11-L12-L11-hétéroarylène,
    où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements L13 identiques ou différents, et/ou peuvent porter un ou plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arylène et chaque hétéroarylène peuvent porter un ou plusieurs radicaux RQc identiques ou différents, où
    L10 revêt l'une des significations indiquées pour L2 ;
    L11 revêt l'une des significations indiquées pour L1 ;
    L12 revêt l'une des significations indiquées pour L3 ;
    L13 revêt l'une des significations indiquées pour L4 ;
    ou
    Q si deux parmi les indices a, b ou c valent chacun 1 et l'indice restant vaut 0, la somme de a+b+c étant de 2,
    est un bras de liaison divalent, qui est choisi parmi C1-C30-alkylène, C2-C30-alcénylène, C3-C16-cycloalkylène, hétérocycloalkylène, C6-C20-arylène, hétéroarylène, C1-C30-alkylène-L10, C2-C30-alcénylène-L10, C3-C16-cycloalkylène-L11-C3-C16-cycloalkylène, C3-C16-cycloalkylène-L11-hétérocycloalkylène, C3-C16-cycloalkylène-L11-C6-C20-arylène, C3-C16-cycloalkylène-L11-hétéroarylène, C6-C20-arylène-L11-C6-C20-arylène, C6-C20-arylène-L11-hétéroarylène, hétéroarylène-L11-hétéroarylène, C3-C16-cycloalkylène-L11-L12-L11-C3-C16-cycloalkylène, C3-C16-cycloalkylène-L11-L12-L11-C6-C20-arylène, C3-C16-cycloalkylène-L11-L12-L11-hétérocycloalkylène, C3-C16-cycloalkylène-L11-L12-L11-hétéroarylène, C6-C20-arylène-L11-L12-L11-C6-C20-arylène, C6-C20-arylène-L11-L12-L11-hétéroarylène, et hétéroarylène-L11-L12-L11-hétéroarylène,
    où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements L13 identiques ou différents, et/ou peuvent porter un ou plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arylène et chaque hétéroarylène peuvent porter un ou plusieurs radicaux RQc identiques ou différents, où
    L10 revêt l'une des significations indiquées pour L2 ;
    L11 revêt l'une des significations indiquées pour L1 ;
    L12 revêt l'une des significations indiquées pour L3 ;
    L13 revêt l'une des significations indiquées pour L4 ;
    ou
    Q si la somme de a+b+c=3,
    est un bras de liaison trivalent, qui est choisi parmi C1-C30-alcanetriyle, C2-C30-alcènetriyle, C3-C16-cycloalcanetriyle, hétérocycloalcanetriyle, C6-C20-arènetriyle, hétéroarènetriyle, C1-C30-alcanetriyl-L14-L15, C2-C30-alcèrietriyl-L14-L15, C1-C30-alkylène-L14-L16, C2-C30-alcènetriyl-L14-L15, C2-C30-alcénylène-L14-L16, C3-C16-cycloalcanetriyl-L14-L11-C3-C16-cycloalkylène, C3-C16-cycloalcanetriyl-L14-L15-C6-C20-arylène, C6-C20-arènetriyl-L14-L15-C6-C20-arylène, et C6-C20-arylène-L14-L15-C3-C16-cycloalcanetriyle,
    où chaque alcanetriyle, chaque alkylène, chaque alcènetriyle et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements L17 identiques ou différents et/ou peuvent porter un ou plusieurs radicaux RQa identiques ou différents ;
    où chaque cycloalcanetriyle, chaque cycloalkylène, chaque hétérocycloalcanetriyle et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux RQb identiques ou différents,
    où chaque arènetriyle, chaque arylène, chaque hétéroarènetriyle et chaque hétéroarylène peuvent porter un ou plusieurs radicaux RQc identiques ou différents, où
    L14 revêt l'une des significations indiquées pour L1 ;
    L15 revêt l'une des significations indiquées pour L2 ;
    L16 est C6-C20-arènetriyle, hétéroarènetriyle, C3-C20-cycloalcanetriyle ou hétérocycloalcanetriyle, où cycloalcanetriyle et hétérocycloalcanetriyle peuvent être interrompus par un ou plusieurs CO, et/ou peuvent être substitués par un ou plusieurs radicaux RL16b identiques ou différents ;
    où arènetriyle et hétéroarènetriyle peuvent être substitués par un ou plusieurs radicaux RL16c identiques ou différents, où
    RL16b revêt l'une des significations indiquées pour RL2b ;
    RL16c revêt l'une des significations indiquées pour RL2c ;
    L17 revêt l'une des significations indiquées pour L4 ;
    Q si la somme de a+b+c=4,
    est un bras de liaison tétravalent, qui est choisi parmi C1-C30-alcanetétrayle qui peut être interrompu par un ou plusieurs groupements L18 identiques ou différents et/ou peut porter un ou plusieurs radicaux RQa identiques ou différents ; où
    L18 revêt l'une des significations données pour L17 ;
    Q si la somme de a+b+c=6,
    est un bras de liaison hexavalent qui est choisi parmi C2-C30-alcanehexayle qui peut être interrompu par un ou plusieurs groupements L19 identiques ou différents et/ou peut porter un ou plusieurs radicaux RQa identiques ou différents ; où
    L19 revêt l'une des significations données pour L17 ;
    R1 est C1-C20-alkyle, C2-C20-alcényle, C2-C20-alcynyle, C3-C20-cycloalkyle, hétérocyclyle, C6-C20-aryle, hétéroaryle, C1-C20-alcanoyle, C3-C20-cycloalcanoyle, C2-C20-alcénoyle, C6-C20-aroyle, CSNR12R13, C(O)OR9 ou CSOR9,
    où C1-C20-alkyle, C2-C20-alcényle et C2-C20-alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO, et/ou peuvent porter un ou plusieurs radicaux R1a identiques ou différents,
    où C3-C20-cycloalkyle et hétérocyclyle peuvent être interrompus par un ou plusieurs groupements CO, et où C3-C20-cycloalkyle peut porter un ou plusieurs radicaux R1b identiques ou différents,
    où C6-C20-aryle et hétéroaryle peuvent porter un ou plusieurs radicaux R1c identiques ou différents,
    où C1-C20-alcanoyle et C2-C20-alcénoyle peuvent porter un ou plusieurs radicaux R1a identiques ou différents,
    où C3-C20-cycloalcanoyle peut porter un ou plusieurs radicaux R1b identiques ou différents,
    où C6-C20-aroyle peut porter un ou plusieurs radicaux R1d identiques ou différents,
    où
    R1a est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C20-cycloalkyle qui peut être interrompu par un ou plusieurs groupements CO, hétérocyclyle qui peut être interrompu par un ou plusieurs groupements CO, hétéroaryle et C6-C10-aryle, où les quatre radicaux susmentionnés peuvent porter un ou plusieurs radicaux R1aa identiques ou différents, où
    R1aa est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-alkyle qui peut être interrompu par un ou plusieurs groupements choisis parmi CO, O,S, C(O)O, OC(O), C(O)S et SC(O), C1-C12-halogénoalkyle, C1-C12-hydroxyalkyle, C2-C12-alcényle, F, Cl, Br, I, NO2, SR4, OR5, NR6R7, COR8, COOR9 et CONR10R11 ;
    R1b est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C1-C12-alkyle, C1-C12-hydroxyalkyle, C1-C12-halogénoalkyle, C2-C12-alcényle, hétéroaryle et C6-C10-aryle, où les deux radicaux susmentionnés peuvent porter un ou plusieurs radicaux R1ba identiques ou différents, où
    R1ba revêt l'une des significations indiquées pour R1aa ;
    R1c est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, C1-C12-hydroxyalkyle, C2-C12-alcényle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11,phényle, hétéroaryle, hétérocyclyle et C3-C10-cycloalkyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou deux groupements C=O et où phényle, hétéroaryle, hétérocyclyle et C3-C10-cycloalkyle peuvent porter un ou plusieurs radicaux R1ca identiques ou différents, où
    R1ca revêt l'une des significations indiquées pour R1aa ;
    R1d est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-halogénoalkyle, C1-C12-hydroxyalkyle, C2-C12-alcényle, F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C20-cycloalkyle qui peut être interrompu par un ou plusieurs groupements CO, hétérocyclyle qui peut être interrompu par un ou plusieurs groupements CO, C6-C10-aryle et hétéroaryle, où les quatre radicaux susmentionnés peuvent porter un ou plusieurs radicaux R1da, où
    R1da revêt l'une des significations indiquées pour R1aa ; ou
    si b vaut 2, 3, 4 ou 6 et/ou c vaut 2, 3, 4 ou 6, deux radicaux R1 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes, ou
    si b vaut 2, 3, 4 ou 6, au moins un groupement -X-R1 peut être lié à un atome de carbone ou un atome d'azote de Q via un groupement de pontage divalent ayant de 1 à 10 atomes entre les liaisons flanquantes,
    R2 est hydrogène, SR4, OR5, NR1R14, COR8, SO2R4, COOR9, CONR10R11, SO2NR10R11, PO (OR9)2, CN, C1-C16-alkyle, C2-C20-alcényle, C2-C20-alcynyle, C3-C20-cycloalkyle, hétérocyclyle, C6-C20-aryle, hétéroaryle, C1-C20-alcanoyle, C2-C20-alcénoyle, C3-C20-cycloalcanoyle, C6-C20-aroyle ou un groupement E,
    où C1-C16-alkyle, C2-C20-alcényle et C2-C20-alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO, et/ou peuvent porter un ou plusieurs radicaux R2a identiques ou différents,
    où C3-C20-cycloalkyle et hétérocyclyle peuvent être interrompus par un ou plusieurs groupements CO, et/ou peuvent porter un ou plusieurs radicaux R2b identiques ou différents,
    où C6-C20-aryle et hétéroaryle peuvent porter un ou plusieurs radicaux R2c identiques ou différents,
    où C1-C20-alcanoyle et C2-C20-alcénoyle peuvent porter un ou plusieurs radicaux R2a identiques ou différents,
    où C3-C20-cycloalcanoyle peut porter un ou plusieurs radicaux R2b identiques ou différents,
    où C6-C20-aroyle peut porter un ou plusieurs radicaux R2d identiques ou différents, où
    R2a est choisi indépendamment les uns des autres parmi F, Cl, Br, I, CN, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C3-C20-cycloalkyle qui peut être interrompu par un ou plusieurs groupements CO, hétérocyclyle qui peut être interrompu par un ou plusieurs groupements CO, hétéroaryle et C6-C10-aryle, où les quatre radicaux susmentionnés peuvent porter un ou plusieurs radicaux R2aa identiques ou différents, où
    R2aa est choisi indépendamment les uns des autres parmi C1-C12-alkyle, C1-C12-alkyle qui peut être interrompu par un ou plusieurs groupements choisis parmi CO, O,S, C(O)O, OC(O), C(O)S et SC(O), C1-C12-halogénoalkyle, C1-C12-hydroxyalkyle, C2-C12-alcényle, phényle, F, Cl, Br, I, CN, NO2, SR4, OR5, NR6R7, COR8, COOR9 et CONR10R11 ;
    R2b revêt l'une des significations indiquées pour R1b ;
    R2c revêt l'une des significations indiquées pour R1c ;
    R2d revêt l'une des significations indiquées pour R1d ;
    E est choisi parmi
    Figure imgb0346
    Figure imgb0347
    Figure imgb0348
     où
    # est le point de fixation au reste de la molécule ;
    d vaut 0, 1, 2, 3 ou 4 ;
    e vaut 0, 1, ou 2 ;
    f vaut 0, 1, ou 2 ;
    g vaut 0, 1, 2, 3 ou 4 ;
    R2e revêt l'une des significations indiquées pour R2c ;
    R2f est C1-C20-alkylène-COO-, C2-C20-alcénylène-COO-, C2-C20-alcynylène-COO-, C3-C20-cycloalkylène-COO-, hétérocycloalkylène-COO-, C6-C20-arylène-COO-, hétéroarylène-COO-, C1-C20-alkylène-S(O2)O-, C2-C20-alcénylène-S(O2)O-, C2-C20-alcynylène-S(O2)O-, C3-C20-cycloalkylène-S(O2)O-, hétérocycloalkylène-S(O2)O-, C6-C20-arylène-S(O2)O-, hétéroarylène-S(O2)O-, C1-C20-alkylène-OS(O2)O-, C2-C20-alcénylène-OS(O2)O-, C2-C20-alcynylène-OS(O2)O-, C3-C20-cycloalkylène-OS (O2)O-, hétérocycloalkylène-OS (O2)O-, C6-C20-arylène-OS(O2)O- ou hétéroarylène-OS(O2)O-,
    où chaque alkylène, chaque alcényle et chaque alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO, et/ou peuvent porter un ou plusieurs radicaux R2a identiques ou différents,
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou deux groupements CO et/ou peuvent porter un ou plusieurs radicaux R2b identiques ou différents,
    où chaque arylène et chaque hétéroarylène peuvent porter un ou plusieurs radicaux R2c,
    An- est Cl-, Br-, I-, SCN-, BF4 -, PF6 -, ClO4 -, SbF6 -, AsF6 -, C1-C20-alkyl-COO-, C1-C20-alkyl-S(O)2O-, C1-C20-alkyl-OS(O)2O-, C6-C20-aryl-COO-, C6-C20-aryl-S(O)2O- ou C6-C20-aryl-OS(O)2O-, où le motif aryle des trois radicaux susmentionnés peut être substitué par 1, 2, 3 ou 4 C1-C20-alkyle identiques ou différents ; ou
    -R2 conjointement avec -X-R1 peut être X-(C1-C20-alkylène)-Y, X-(C2-C20-alcénylène) -Y, X-(C3-C20-cycloalkylène)-Y, X-(hétérocycloalkylène)-Y, X-(o-phénylène)-Y, X-(o-xylylène) -Y, X-(o-phénylène-C1-C12-alkylène)-Y, X-(C1-C12-alkylène-o-phénylène)-Y, X-(O-C1-C20-alkylène)-Y, X-(S-C1-C20-alkylène)-Y ou X-(N(R6)-C1-C20-alkylène)-Y, Y étant fixé à l'atome de carbone d'oxime portant X,
    où chaque alkylène et alcénylène peuvent comprendre un ou plusieurs groupements identiques ou différents choisis parmi O,S, NR6 et CO et/ou peuvent être substitués par un ou plusieurs radicaux R2g,
    où cycloalkylène et hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent éventuellement être substitués par un ou plusieurs radicaux R2h identiques ou différents,
    où chaque phénylène et le motif phénylène de o-xylylène peuvent être substitués par un ou plusieurs radicaux R2h identiques ou différents, où
    Y est O,S, NR14, CO, SC(O), OC(O), C(O)O, NR10C(O), C(O)NR10, NR10SO2 ou une liaison simple ;
    R2g est choisi indépendamment les uns des autres parmi F, Cl, Br, I, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, hétéroaryle et C6-C10-aryle où les deux radicaux susmentionnés peuvent porter un ou plusieurs radicaux R2ga, où
    R2ga est phénoxy ou revêt l'une des significations indiquées pour R1aa ;
    R2h est choisi indépendamment les uns des autres parmi F, Cl, Br, I, SR4, OR5, NR6R7, COR8, COOR9, CONR10R11, C1-C12-alkyle, C1-C12-halogénoalkyle, hétéroaryle et C6-C10-aryle, où les deux radicaux susmentionnés peuvent porter un ou plusieurs radicaux R2ha, où R2ha revêt l'une des significations indiquées pour R1aa ;
    ou si X est S, -R2 est tel que défini ci-dessus ou -R2 conjointement avec -S-R1 est S-C(S)-NR12-C(O) ou S-C(=NOR15)-C(O)-NR12-C(O), où R15 est hydrogène ou phénylsulfonyle où le motif phényle peut être substitué par C1-C4-alkyle ou C1-C4-alcoxy ; ou
    si a vaut 2, 3, 4 ou 6 et/ou c vaut 2, 3, 4 ou 6, deux radicaux R2 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes ;
    R3 est C1-C20-alkyle, C2-C20-alcényle, C2-C20-alcynyle, C3-C20-cycloalkyle, hétérocyclyle, C6-C20-aryle ou hétéroaryle,
    où C1-C20-alkyle, C2-C20-alcényle et C2-C20-alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO, et/ou peuvent porter un ou plusieurs radicaux R3a identiques ou différents,
    où C3-C20-cycloalkyle et hétérocyclyle peuvent être interrompus par un ou plusieurs groupements CO, et/ou peuvent porter un ou plusieurs radicaux R3b identiques ou,
    où C6-C20-aryle et hétéroaryle peuvent porter un ou plusieurs identiques ou radicaux R3c, où
    R3a revêt l'une des significations indiquées pour R2a ;
    R3b revêt l'une des significations indiquées pour R1b ;
    R3c revêt l'une des significations indiquées pour R1c ; ou
    -X-R1 et R3 peuvent former ensemble un radical divalent choisi parmi X-(C1-C20-alkylène)-Z, X-(C2-C20-alcénylène)-Z, X-(C3-C20-cycloalkylène)-Z, X-(hétérocycloalkylène)-Z, X-(o-phénylène)-Z, X-(o-xylylène)-Z, X-(C0-C12-alkylène-hétéroarylène-C0-C12-alkylène)-Z ; X-(o-phénylène-C1-C12-alkylène)-Z, X-(C1-C12-alkylène-o-phénylène) -Z et S-C(S) -NR12-C(O),
    où Z est fixé à l'atome de soufre du groupement sulfonate, où chaque alkylène et chaque alcénylène peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi O, S, NR6 et CO, et/ou peuvent être substitués par un ou plusieurs radicaux R3g,
    où chaque cycloalkylène et chaque hétérocycloalkylène peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent éventuellement être substitués par un ou plusieurs radicaux R3h identiques ou différents,
    où chaque phénylène et le motif phénylène de o-xylylène peuvent être substitués par un ou plusieurs radicaux R3h identiques ou différents, où
    R3g revêt l'une des significations indiquées pour R2g ;
    R3h revêt l'une des significations indiquées pour R2h ; et
    Z est O, S, NR14, CO, OC(O), SC(O), C(O)O, NR10C(O), C(O)NR10, NR10(SO2) ou une liaison simple ;
    R4 est choisi indépendamment les uns des autres parmi hydrogène, C1-C20-alkyle, C2-C12-alcényle,
    C3-C10-cycloalkyle, hétérocyclyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou plusieurs groupements C=O,
    C1-C20-alkyle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(C1-C8-alkyl)- et CO, et/ou peut porter un ou plusieurs radicaux R4a identiques ou différents,
    C2-C12-alcényle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, et -N(C1-C8-alkyl)-,
    - (CH2CH2O)mH, m valant 1-20,
    - (CH2CH2O)n(CO)-(C1-C8-alkyl), n valant 1-20,
    C2-C8-alcanoyle, C3-C6-alcénoyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, OH ou C1-C6-alcoxy,
    benzoyle qui peut être substitué par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, C1-C6-alkyle, OH et C1-C6-alcoxy,
    phényle et naphtyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R4c identiques ou différents,
    ou phényle ou naphtyle forment un cycle de 5 ou 6 chaînons avec le cycle phényle auquel SR4 est fixé via une liaison simple, C1-C4-alkylène, O, S, NR6 ou CO, où R4a est choisi indépendamment les uns des autres parmi F, Cl, Br, I, C3-C10-cycloalkyle, hétérocyclyle, phényle, OH, SH, CN, C3-C6-alcénoxy, OCH2CH2CN, OCH2CH2(CO)O(C1-C8-alkyl), O(CO)-(C1-C8-alkyl), O(CO)-phényle, (CO)OH et (CO)O(C1-C8-alkyl);
    R4c est choisi indépendamment les uns des autres parmi F, Cl, Br, I, C1-C12-alkyle, C1-C12-halogénoalkyle, C1-C12-alcoxy, phényl-C1-C3-alcoxy, phénoxy, C1-C12-alkylsulfanyle, phénylsulfanyle, -(CO)O(C1-C8-alkyl), (CO)N(C1-C8-alkyl)2 et phényle ;
    R5 est choisi indépendamment les uns des autres parmi hydrogène, C1-C20-alkyle, C2-C12-alcényle, C3-C10-cycloalkyle, hétérocyclyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou deux groupements C=O,
    C1-C20-alkyle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(C1-C8-alkyl)- et CO, et/ou peut porter un ou plusieurs radicaux R5a identiques ou différents,
    C2-C12-alcényle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, et -N(C1-C8-alkyl)-,
    - (CH2CH2O)mH, m valant 1-20,
    - (CH2CH2O)n(CO)-(C1-C8-alkyl), n valant 1-20,
    C2-C8-alcanoyle, C3-C6-alcénoyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, OH et C1-C6-alcoxy,
    C2-C8-alcanoyle, qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O- et -S- et peut être substitué par un ou plusieurs radicaux identiques ou différents choisis parmi hydroxyaminylène (=N-O), F, Cl, Br, I, OH et C1-C6-alcoxy,
    benzoyle qui peut être substitué par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, C1-C6-alkyle, OH et C1-C6-alcoxy,
    phényle et naphtyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R5c identiques ou différents,
    ou phényle ou naphtyle forment un cycle de 5 ou 6 chaînons avec le cycle phényle auquel OR5 est fixé via une liaison simple, C1-C4-alkylène, O, S, NR6 ou CO,
    où R5a revêt l'une des significations indiquées pour R4a ;
    R5c revêt l'une des significations indiquées pour R4c ;
    R6, R10 et R12 sont choisis indépendamment les uns des autres parmi hydrogène, OR5, C1-C20-alkyle, C2-C12-alcényle,
    C3-C10-cycloalkyle, hétérocyclyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou deux groupements C=O,
    C1-C20-alkyle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(C1-C8-alkyl)- et CO, et/ou peut porter un ou plusieurs radicaux R6a identiques ou différents,
    C2-C12-alcényle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, et -N(C1-C8-alkyl)-,
    -(CH2CH2O)oH, o valant 1-20,
    -(CH2CH2O)p(CO)-(C1-C8-alkyl), p valant 1-20,
    C2-C8-alcanoyle, C3-C6-alcénoyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, OH et C1-C6-alcoxy,
    benzoyle qui peut être substitué par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, C1-C6-alkyle, -OH et C1-C6-alcoxy,
    phényle et naphtyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R6c identiques ou différents, où
    R6a revêt l'une des significations indiquées pour R4a ;
    R6c revêt l'une des significations indiquées pour R4c ; ou
    deux radicaux R6 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes ; ou
    deux radicaux R10 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes ; ou
    deux radicaux R12 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes ;
    R7, R11 et R13 sont choisis indépendamment les uns des autres parmi OR5, C1-C20-alkyle, C2-C12-alcényle,
    C3-C10-cycloalkyle, hétérocyclyle, où dans les deux radicaux susmentionnés un ou deux groupements CH2 peuvent être remplacés par un groupement C=O,
    C1-C20-alkyle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(C1-C8-alkyl)- et CO, et/ou peut porter un ou plusieurs radicaux R7a identiques ou différents,
    C2-C12-alcényle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, et -N(C1-C8-alkyl)-,
    - (CH2CH2O)qH, q valant 1-20,
    - (CH2CH2O)r(CO)-(C1-C8-alkyl), r valant 1-20, C2-C8-alcanoyle, C3-C6-alcénoyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, OH et C1-C6-alcoxy,
    benzoyle qui peut être substitué par un ou plusieurs radicaux identiques ou différents choisis parmi F, Cl, Br, I, C1-C6-alkyle, OH et C1-C6-alcoxy,
    phényle et naphtyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R7c identiques ou différents, où
    R7a revêt l'une des significations indiquées pour R4a ;
    R7c revêt l'une des significations indiquées pour R4c ;
    ou
    R6 et R7, conjointement avec l'atome d'azote auquel ils sont fixés, forment un hétérocycle azoté de 5, 6 ou 7 chaînons saturé pouvant posséder un autre hétéroatome ou groupement hétéroatomique choisi dans le groupe constitué par CO, O, S et N(C1-C8-alkyl) comme chaînon et pouvant porter 1, 2, 3 ou 4 C1-C4-alkyle ; ou
    R10 et R11, conjointement avec l'atome d'azote auquel ils sont fixés, forment un hétérocycle azoté de 5, 6 ou 7 chaînons saturé pouvant posséder un autre hétéroatome ou groupement hétéroatomique choisi dans le groupe constitué par CO, O, S et N(C1-C8-alkyl) comme chaînon et pouvant porter 1, 2, 3 ou 4 C1-C4-alkyle ; ou
    R12 et R13, conjointement avec l'atome d'azote auquel ils sont fixés, forment un hétérocycle azoté de 5, 6 ou 7 chaînons saturé pouvant posséder un autre hétéroatome ou groupement hétéroatomique choisi dans le groupe constitué par CO, O, S et N(C1-C8-alkyl) comme chaînon et pouvant porter 1, 2, 3 ou 4 C1-C4-alkyle ;
    R8 est choisi indépendamment les uns des autres parmi hydrogène, C1-C20-alkyle, C2-C12-alcényle,
    C3-C10-cycloalkyle, hétérocyclyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou plusieurs groupements C=O,
    C1-C20-alkyle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(C1-C8-alkyl)- et CO, et/ou peut porter un ou plusieurs radicaux R8a identiques ou différents,
    C2-C12-alcényle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, et -N(C1-C8-alkyl)-,
    - (CH2CH2O)sH, s valant 1-20,
    - (CH2CH2O)t(CO)-(C1-C8-alkyl), t valant 1-20,
    C6-C20-aryle et hétéroaryle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R8c identiques ou différents, où
    R8a revêt l'une des significations indiquées pour R4a ;
    R8c revêt l'une des significations indiquées pour R4c ;
    R9 est choisi indépendamment les uns des autres parmi hydrogène, C1-C20-alkyle, C2-C12-alcényle,
    C3-C10-cycloalkyle, hétérocyclyle, où les deux radicaux susmentionnés peuvent être interrompus par un ou plusieurs groupements C=O,
    C1-C20-alkyle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(C1-C8-alkyl)- et CO, et/ou peut porter un ou plusieurs radicaux R9a identiques ou différents,
    C2-C12-alcényle qui est interrompu par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, et -N(C1-C8-alkyl)-,
    - (CH2CH2O)uH, u valant 1-20,
    - (CH2CH2O)v(CO)-(C1-C8-alkyl), v valant 1-20,
    phényle et naphtyle, où les deux radicaux susmentionnés peuvent être substitués par un ou plusieurs radicaux R9c identiques ou différents, où
    R9a revêt l'une des significations indiquées pour R4a ;
    R9c revêt l'une des significations indiquées pour R4c ;
    R14 est C1-C20-alkyle, C2-C20-alcényle, C2-C20-alcynyle, C3-C20-cycloalkyle, hétérocyclyle, C6-C20-aryle, hétéroaryle, C1-C20-alcanoyle, C2-C20-alcénoyle, C3-C20-cycloalcanoyle, C6-C20-aroyle, CSNR12R13 ou CSOR9,
    où C1-C20-alkyle, C2-C20-alcényle et C2-C20-alcynyle peuvent être interrompus par un ou plusieurs groupements identiques ou différents choisis parmi -O-, -S-, -N(R6)- et CO et/ou peuvent porter un ou plusieurs radicaux R14a identiques ou différents,
    où C3-C20-cycloalkyle et hétérocyclyle peuvent être interrompus par un ou plusieurs groupements CO et/ou peuvent porter un ou plusieurs radicaux R14b identiques ou différents,
    où C6-C20-aryle, hétéroaryle peuvent porter un ou plusieurs identiques ou radicaux R14c,
    où C1-C20-alcanoyle, C2-C20-alcénoyle peuvent porter un ou plusieurs radicaux R14a identiques ou différents,
    où C3-C20-cycloalcanoyle peut porter un ou plusieurs radicaux R14b identiques ou différents,
    où C6-C20-aroyle peut porter un ou plusieurs radicaux R14d identiques ou différents, où
    R14a revêt l'une des significations indiquées pour R2a ;
    R14b revêt l'une des significations indiquées pour R1b ;
    R14c revêt l'une des significations indiquées pour R1c ;
    R14d revêt l'une des significations indiquées pour R1d ;
    ou
    R1 conjointement avec R14 peut être un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes ;
    ou deux radicaux R14 peuvent être ensemble un groupement de pontage divalent ayant de 1 à 20 atomes entre les liaisons flanquantes,
    à l'exception des composés de formule I dans lesquels
    - si a vaut 1, b=c=0, X-R1 est phénylsulfanyle et R2 est 5-(2-chloro-4-trifluorométhyl-phénoxy)-2-nitrophényle, R3 est méthyle ;
    - si a vaut 1, b=c=0, X-R1 et R2 sont ensemble N(CH3)-éthylène-N(CH3), R3 est phényle ou p-tolyle ;
    - si a vaut 1, b=c=0, X-R1 et R2 sont ensemble CON(benzyl)-éthylène-S, R3 est phényle, tolyle ou fluorophényle ;
    - si a vaut 1, b=c=0, X-R1 et R2 sont ensemble N(CH3)-éthylène-O, R3 est p-tolyle ;
    - si a vaut 1, b=c=0, X-R1 et R2 sont ensemble N(CH3)-o-phénylène-S, R3 est p-tolyle ;
    - si a vaut 1, b=c=0, X-R1 et R2 sont ensemble N(CH3)-propylène, R3 est p-tolyle ;
    - si a vaut 1, b=c=0, X-R1 est SCH3 et R2 est propyle ou allyle, R3 est p-tolyle ;
    - si a vaut 1, b=c=0, X-R1 est SCH3 ou SC2H5 et R2 est méthyle ou éthyle, R3 est p-tolyle ;
    - si a vaut 1, b=c=0, X-R1 est N(CH3)CH2CH2OH et R2 est phényle, R3 est p-tolyle ;
    - si a vaut 1, b=c=0, X-R1 est pipéridino ou N(C2H5)2 et R2 est CN, R3 est p-tolyle ;
    - si a vaut 1, b=c=0, X-R1 est N(CH3)2 et R2 est 2,6-dichlorophényle, R3 est méthyle ;
    - si a vaut 1, b=c=0, X-R1 est SC(S)NR12R13, où NR12R13 est N(CH3)2, N(C2H5)2, morpholino, pipéridino ou pyrrolidino et R2 est phényle, 3-nitrophényle, 4-nitrophényle ou 4-chlorophényle, R3 est méthyle, et
    - si a vaut 1, b=c=0, X-R1 et R2 sont ensemble S-(1,2-phénylène)-CO et R3 est phényle ;
    et de même à l'exception des composés de formule I dans lesquels
    - si a vaut 1, b=c=0, X = SO2, R1 est phényle ou 2-chlorophényle, R2 est diméthylaminocarbonyle et R3 est 4-méthylphényle ;
    - si a vaut 1, b=c=0, X= SO2, R1 est 2-chlorophényle, R2 est diméthylaminocarbonyle et R3 est 4-chlorophényle ;
    - si a vaut 1, b=c=0, X= SO2, R1 est 2-thiényle, R2 est cyano et R3 est 4-chlorophényle ;
    - si a vaut 1, b=c=0, X= SO2, R1 est 4-chlorophényle, R2 est cyano et R3 est 3,5-bis(trifluorométhyl)phényle ;
    - le [cyano(p-tolylsulfonyl)méthylène]amino-méthanesulfonate ;
    - le [1-[(6-chloro-3-pyridyl)méthyl]pyrrolidin-2-ylidène]amino-méthanesulfonate ;
    - le [1-[(6-chloro-3-pyridyl)méthyl]pyrrolidin-2-ylidène]amino-éthanesulfonate ; et
    - le [1-[(6-chloro-3-pyridyl)méthyl]pyrrolidin-2-ylidène]amino-4-méthylbenzènesulfonate.
EP12701354.8A 2011-01-28 2012-01-27 Composition polymérisable comprenant un sulfonate d'oxime en tant qu'agent de durcissement thermique Not-in-force EP2668156B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP12701354.8A EP2668156B1 (fr) 2011-01-28 2012-01-27 Composition polymérisable comprenant un sulfonate d'oxime en tant qu'agent de durcissement thermique

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201161437024P 2011-01-28 2011-01-28
EP11152582 2011-01-28
EP12701354.8A EP2668156B1 (fr) 2011-01-28 2012-01-27 Composition polymérisable comprenant un sulfonate d'oxime en tant qu'agent de durcissement thermique
PCT/EP2012/051297 WO2012101245A1 (fr) 2011-01-28 2012-01-27 Composition polymérisable comprenant un sulfonate d'oxime en tant qu'agent de durcissement thermique

Publications (2)

Publication Number Publication Date
EP2668156A1 EP2668156A1 (fr) 2013-12-04
EP2668156B1 true EP2668156B1 (fr) 2018-10-31

Family

ID=44801919

Family Applications (1)

Application Number Title Priority Date Filing Date
EP12701354.8A Not-in-force EP2668156B1 (fr) 2011-01-28 2012-01-27 Composition polymérisable comprenant un sulfonate d'oxime en tant qu'agent de durcissement thermique

Country Status (6)

Country Link
US (3) US9310677B2 (fr)
EP (1) EP2668156B1 (fr)
JP (2) JP5955339B2 (fr)
KR (1) KR101897842B1 (fr)
CN (1) CN103443072B (fr)
WO (1) WO2012101245A1 (fr)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5521848B2 (ja) * 2010-07-21 2014-06-18 デクセリアルズ株式会社 異方性導電フィルム、接続構造体及びそれらの製造方法
WO2012029758A1 (fr) * 2010-08-30 2012-03-08 富士フイルム株式会社 Composition de résine photosensible, composé de sulfonate d'oxime, procédé de formation d'un film durci, film durci, dispositif d'affichage el organique et dispositif d'affichage à cristaux liquides
JP6530410B2 (ja) 2013-09-10 2019-06-12 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ オキシムエステル光開始剤
CN104624124B (zh) * 2013-11-07 2017-02-08 中国科学院化学研究所 液晶微胶囊及其制备方法
JP6333947B2 (ja) * 2014-02-20 2018-05-30 富士フイルム株式会社 感光性樹脂組成物、硬化物及びその製造方法、樹脂パターン製造方法、硬化膜、液晶表示装置、有機ｅｌ表示装置、赤外線カットフィルター、並びに、固体撮像装置
CN103966851B (zh) * 2014-05-22 2016-08-24 安徽工程大学 一种功能性aopan纳米纤维及其制备方法
KR20170048422A (ko) * 2014-08-29 2017-05-08 바스프 에스이 옥심 술포네이트 유도체
JP6671381B2 (ja) 2015-02-02 2020-03-25 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 潜在酸およびそれらの使用
TW201723096A (zh) * 2015-12-31 2017-07-01 奇美實業股份有限公司 感光性樹脂組成物及其應用
US10933389B2 (en) * 2017-07-28 2021-03-02 Swimc Llc Tinting water-borne and solvent-borne paints and stains with powdered colorants
CN109307898B (zh) * 2017-07-28 2021-06-29 深圳市柯达科电子科技有限公司 一种因不同材料变更反射的方法
US10934151B2 (en) * 2017-07-28 2021-03-02 Swimc Llc Tinting water-borne and solvent-borne paints and stains with water-only colorants
CN111051982B (zh) * 2017-09-28 2023-04-25 东丽株式会社 有机el显示装置以及像素分割层和平坦化层的形成方法
KR102548106B1 (ko) * 2017-10-11 2023-06-27 도레이 카부시키가이샤 감광성 도전 페이스트 및 도전 패턴 형성용 필름
KR102333186B1 (ko) * 2018-08-17 2021-11-29 주식회사 엘지화학 필름 인쇄 가능한 자외선 경화형 잉크 조성물, 이를 이용한 베젤패턴의 제조방법, 이에 따라 제조한 베젤패턴 및 이를 포함하는 디스플레이 기판
US20220121113A1 (en) 2019-01-23 2022-04-21 Basf Se Oxime ester photoinitiators having a special aroyl chromophore
CN112420499B (zh) * 2019-08-23 2022-12-20 天津大学 图案化氧化铝介电层和栅极及其制备方法和应用
TW202130674A (zh) * 2020-01-20 2021-08-16 日商富士軟片股份有限公司 著色樹脂組成物、膜、濾色器、固體攝像元件及圖像顯示裝置
WO2021175855A1 (fr) 2020-03-04 2021-09-10 Basf Se Photo-initiateurs à base d'ester d'oxime
CN111499778B (zh) * 2020-04-29 2021-10-01 中国科学技术大学 抗菌聚烯烃材料及其制备方法和用途
CN115368341B (zh) * 2021-05-20 2024-01-26 常州强力先端电子材料有限公司 肟磺酸酯化合物、含其的抗蚀剂组合物、电子器件及应用
CN115368340B (zh) * 2021-05-20 2024-01-26 常州强力先端电子材料有限公司 肟磺酸酯光产酸剂、含其的抗蚀剂组合物、电子器件及应用
CN115611874A (zh) * 2021-07-16 2023-01-17 常州强力先端电子材料有限公司 肟磺酸酯光酸、含其的抗蚀剂组合物、电子器件及应用
JP2024503455A (ja) * 2021-10-08 2024-01-25 エルジー・ケム・リミテッド 硬化性組成物
CN115611782A (zh) * 2022-10-15 2023-01-17 瑞红(苏州)电子化学品股份有限公司 高产酸肟磺酸酯类光产酸剂及其抗蚀剂组合物应用

Family Cites Families (72)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4278613A (en) 1978-08-28 1981-07-14 Ciba-Geigy Corporation Sulfur-containing oxime compounds, processes for producing them, and their use for protecting cultivated plants
JPS5742009A (en) 1980-08-27 1982-03-09 Matsushita Electric Ind Co Ltd Formation of protective film for color mosaic filter
US4346094A (en) 1980-09-22 1982-08-24 Eli Lilly And Company 3-Aryl-5-isothiazolecarboxylic acids and related compounds used to lower uric acid levels
EP0064091A1 (fr) 1981-05-06 1982-11-10 Allied Corporation Production d'hydrocarbylthioaldoximes en solution aqueuse-méthanolique
JPS59197401A (ja) 1983-04-26 1984-11-09 Nippon Oil & Fats Co Ltd 光重合開始剤
JPS6011409A (ja) 1983-06-30 1985-01-21 Mitsubishi Rayon Co Ltd 歯科用材料
GB8422701D0 (en) 1984-09-07 1984-10-10 Shell Int Research Ether herbicides
GB2180358B (en) 1985-07-16 1989-10-04 Mead Corp Photosensitive microcapsules and their use on imaging sheets
US4977511A (en) 1985-11-20 1990-12-11 The Mead Corporation Photosensitive materials containing ionic dye compound as initiators
JPS6490516A (en) 1987-09-30 1989-04-07 Sumitomo Metal Ind Semiconductor porcelain material
JPH01130103A (ja) 1987-11-16 1989-05-23 Toppan Printing Co Ltd カラーフィルターの製造方法
JPH01134306A (ja) 1987-11-19 1989-05-26 Japan Synthetic Rubber Co Ltd カラーフィルターの製造方法
US4934791A (en) 1987-12-09 1990-06-19 Matsushita Electric Industrial Co., Ltd. Color filter
HU199134B (en) 1987-12-14 1990-01-29 Richter Gedeon Vegyeszet Process for producing new 2,3-thiomorpholinedine-2-oxime derivatives and pharmaceutical compositions comprising same
EP0438123B1 (fr) 1990-01-16 1995-09-13 Showa Denko Kabushiki Kaisha Initiateur de polymérisation utilisable dans l'infrarouge proche
EP0441232A3 (en) 1990-02-09 1992-10-14 Basf Aktiengesellschaft Cationic photopolymerisation process
WO1992003050A1 (fr) * 1990-08-16 1992-03-05 E.I. Du Pont De Nemours And Company Esters fongicides de sulfoneoxime
JP2999274B2 (ja) 1991-01-28 2000-01-17 三菱化学株式会社 エチレン重合体の製造法
JP2794242B2 (ja) 1991-06-25 1998-09-03 富士写真フイルム株式会社 感光性転写材料及び画像形成方法
US5368976A (en) 1992-03-27 1994-11-29 Japan Synthetic Rubber Co., Ltd. Pigment-dispersed color-filter composition comprising an alkali-soluble block copolymer as a binder
JPH0668309A (ja) 1992-08-14 1994-03-11 Matsushita Electric Ind Co Ltd パターン判別用ファジィ推論装置および判別ルール作成装置
JP3218256B2 (ja) 1993-01-29 2001-10-15 東洋インキ製造株式会社 アルカリ現像型感光性着色組成物
EP0645678B1 (fr) 1993-09-24 1998-03-04 Japan Synthetic Rubber Co., Ltd. Composition sensible aux radiations
DE69418826T2 (de) 1993-11-22 1999-10-21 Ciba Specialty Chemicals Holding Inc., Basel Zusammensetzungen zur Herstellung strukturierter Farbbilder und deren Anwendung
TW339421B (en) 1994-09-12 1998-09-01 Sumitomo Kagaku Kk A photoresist composition comprising a polyfunctional vinyl ether compound
US5882843A (en) 1994-11-15 1999-03-16 Hoechst Japan Limited Photosensitive resin composition for color filter production
EP0723167A3 (fr) 1995-01-17 1997-04-02 Mitsubishi Chem Corp Composition photopolymérisable pour filtre chromatique
JPH08305019A (ja) 1995-05-10 1996-11-22 Fuji Photo Film Co Ltd 光重合性組成物
JPH0915857A (ja) 1995-06-29 1997-01-17 Hitachi Chem Co Ltd 着色画像形成材料、これを用いた感光液、感光性エレメント及びカラーフィルタの製造法
JP3564836B2 (ja) 1995-11-22 2004-09-15 Ｊｓｒ株式会社 カラーフィルタ用感放射線性組成物およびカラーフィルタ
JP3587413B2 (ja) 1995-12-20 2004-11-10 東京応化工業株式会社 化学増幅型レジスト組成物及びそれに用いる酸発生剤
JPH09179299A (ja) 1995-12-21 1997-07-11 Fuji Photo Film Co Ltd 感放射線性組成物
DE69620723T2 (de) 1995-12-22 2002-12-05 Mitsubishi Chemical Corp., Tokio/Tokyo Fotopolymerisierbare Zusammensetzung für einen Farbfilter, Farbfilter und Flüssigkristallanzeigevorrichtung
JP3641093B2 (ja) 1996-02-02 2005-04-20 東京応化工業株式会社 緑色カラーフィルタ用感光性組成物及びこれを用いた緑色カラーフィルタの製造方法
JPH09325209A (ja) 1996-06-06 1997-12-16 Fuji Photo Film Co Ltd Ｌｃｄ表示装置用カラーフィルター
JPH1010718A (ja) 1996-06-25 1998-01-16 Hitachi Chem Co Ltd 着色画像形成材料、感光液、感光性エレメント、カラーフィルターの製造法及びカラーフィルター
JPH10171119A (ja) 1996-12-11 1998-06-26 Tokyo Ohka Kogyo Co Ltd 光重合性樹脂組成物、およびこれを用いた色フィルタの製造方法
JP3849950B2 (ja) 1997-02-06 2006-11-22 東京応化工業株式会社 色フィルタ用感光性組成物
JP3829412B2 (ja) 1997-05-28 2006-10-04 Ｊｓｒ株式会社 カラーフィルタ用感放射線性組成物
TW550439B (en) 1997-07-01 2003-09-01 Ciba Sc Holding Ag New oxime sulfonates as latent acids and compositions and photoresists comprising said oxime sulfonates
EP0902327A3 (fr) 1997-09-09 2000-04-05 JSR Corporation Composition sensible aux radiations
JPH11174459A (ja) 1997-12-11 1999-07-02 Hitachi Chem Co Ltd カラー液晶表示装置用スペーサーフィルム
JP3951396B2 (ja) 1997-12-12 2007-08-01 日立化成工業株式会社 樹脂スペーサー形成用感光性フィルム
JP2000081701A (ja) 1998-09-03 2000-03-21 Jsr Corp カラーフィルター保護膜用感放射線性樹脂組成物
EP1033125B1 (fr) 1999-03-03 2003-09-24 Kuraray Co., Ltd. Fixateur pour une prothèse dentaire
ATE330254T1 (de) * 1999-03-03 2006-07-15 Ciba Sc Holding Ag Oximderivate und ihre verwendung als photoinitiatoren
SG78412A1 (en) 1999-03-31 2001-02-20 Ciba Sc Holding Ag Oxime derivatives and the use thereof as latent acids
TWI272451B (en) 2000-09-25 2007-02-01 Ciba Sc Holding Ag Chemically amplified photoresist composition, process for preparation of a photoresist, and use of said chemically amplified photoresist composition
JP4404330B2 (ja) 2001-01-09 2010-01-27 東京応化工業株式会社 光重合性組成物および該組成物を用いたカラーフィルタの製造方法
JP4660986B2 (ja) 2001-06-28 2011-03-30 Ｊｓｒ株式会社 カラー液晶表示装置用感放射線性組成物、およびカラーフィルタ
JP4120437B2 (ja) 2002-03-29 2008-07-16 Ｊｓｒ株式会社 スルホニル構造を有する化合物、それを用いた感放射線性酸発生剤、ポジ型感放射線性樹脂組成物、及びネガ型感放射線性樹脂組成物
JP2003330184A (ja) 2002-05-13 2003-11-19 Fuji Photo Film Co Ltd 着色感光性樹脂組成物及びカラーフィルター
JP2004069754A (ja) 2002-08-01 2004-03-04 Tokyo Ohka Kogyo Co Ltd 光重合性黒色組成物及び黒色パターンの形成方法
BRPI0407605A (pt) 2003-02-19 2006-02-14 Ciba Sc Holding Ag derivados de oxima halogenados e o uso dos mesmos como ácidos latentes
JP4443848B2 (ja) 2003-03-31 2010-03-31 新日鐵化学株式会社 カラーフィルター用レジスト材料及びカラーフィルター
JP3754065B2 (ja) 2003-06-10 2006-03-08 三菱化学株式会社 光重合性組成物及びこれを用いたカラーフィルター
JP4437651B2 (ja) 2003-08-28 2010-03-24 新日鐵化学株式会社 感光性樹脂組成物及びそれを用いたカラーフィルター
CN101805282B (zh) 2004-02-23 2012-07-04 三菱化学株式会社 肟酯化合物、光聚合性组合物和使用该组合物的滤色器
JP4570999B2 (ja) 2004-03-30 2010-10-27 新日鐵化学株式会社 感光性樹脂組成物及びそれを用いたカラーフィルター
JP4448381B2 (ja) 2004-05-26 2010-04-07 東京応化工業株式会社 感光性組成物
EP1768188A1 (fr) 2004-06-01 2007-03-28 Nikon Corporation Procédé de fabrication de dispositif électronique et dispositif electronique
TWI415838B (zh) 2005-12-01 2013-11-21 Ciba Sc Holding Ag 肟酯光起始劑
WO2007071797A1 (fr) 2005-12-19 2007-06-28 Uralita Sistemas De Tuberias, S.A. Systeme distribue de transmission bidirectionnelle d'ondes guidees et/ou irradiees
CN102199119B (zh) 2005-12-20 2014-07-16 西巴控股有限公司 肟酯光引发剂
US20090292039A1 (en) 2006-12-27 2009-11-26 Adeka Corporation Oxime ester compound and photopolymerization initiator containing the same
JP2009086357A (ja) * 2007-09-28 2009-04-23 Fujifilm Corp 感光性樹脂組成物、該組成物を用いるパターンの製造法および電子デバイス
JP5589258B2 (ja) 2008-03-26 2014-09-17 宇部興産株式会社 水硬性組成物およびその硬化体
JP5339781B2 (ja) * 2008-05-30 2013-11-13 富士フイルム株式会社 着色硬化性組成物、カラーフィルタ、及び、固体撮像素子
JP2010015025A (ja) 2008-07-04 2010-01-21 Adeka Corp 特定の光重合開始剤を含有する感光性組成物
JP5685803B2 (ja) 2008-07-24 2015-03-18 Jsr株式会社 感放射線性樹脂組成物および液晶表示素子用スペーサーとその製造法
CN102361896B (zh) 2009-03-23 2015-10-07 巴斯夫欧洲公司 光致抗蚀剂组合物
TW201129561A (en) 2010-01-06 2011-09-01 Univ Gifu Imino derivatives and methods for producing the same, and insecticides containing the same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Also Published As

Publication number Publication date
EP2668156A1 (fr) 2013-12-04
JP2014511400A (ja) 2014-05-15
JP5955339B2 (ja) 2016-07-20
CN103443072B (zh) 2016-05-18
US20160060214A1 (en) 2016-03-03
JP2015212309A (ja) 2015-11-26
WO2012101245A1 (fr) 2012-08-02
CN103443072A (zh) 2013-12-11
US10241399B2 (en) 2019-03-26
KR20140006005A (ko) 2014-01-15
US9310677B2 (en) 2016-04-12
US20130308219A1 (en) 2013-11-21
JP6284511B2 (ja) 2018-02-28
US20190171099A1 (en) 2019-06-06
KR101897842B1 (ko) 2018-09-12

Similar Documents

Publication Publication Date Title
US10241399B2 (en) Polymerizable composition comprising an oxime sulfonate as thermal curing agent
EP3186226B1 (fr) Dérivés de sulfonate d'oxime
EP2411430B1 (fr) Composition de résine photosensible
EP3044208B1 (fr) Photoamorceurs à base d'ester d'oxime
EP1567518B1 (fr) Photo-initiateurs a base d'ester d'oxime comportant des groupes heteroaromatiques
JP2012521573A5 (fr)
KR20010102461A (ko) 옥심 유도체 및 광개시제로서의 이의 용도
WO2015004565A1 (fr) Photoinitiateurs à base d'ester d'oxime
WO2021175855A1 (fr) Photo-initiateurs à base d'ester d'oxime
WO2020152120A1 (fr) Photo-initiateurs à base d'ester d'oxime ayant un chromophore aroyle spécial

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20130828

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20140512

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: GRANT OF PATENT IS INTENDED

INTG Intention to grant announced

Effective date: 20180524

RIN1 Information on inventor provided before grant (corrected)

Inventor name: SAMESHIMA, KAORI

Inventor name: KURA, HISATOSHI

Inventor name: KUNIMOTO, KAZUHIKO

Inventor name: MATSUOKA, YUKI

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE PATENT HAS BEEN GRANTED

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: AT

Ref legal event code: REF

Ref document number: 1059206

Country of ref document: AT

Kind code of ref document: T

Effective date: 20181115

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: DE

Ref legal event code: R096

Ref document number: 602012052835

Country of ref document: DE

REG Reference to a national code

Ref country code: NL

Ref legal event code: MP

Effective date: 20181031

REG Reference to a national code

Ref country code: LT

Ref legal event code: MG4D

REG Reference to a national code

Ref country code: AT

Ref legal event code: MK05

Ref document number: 1059206

Country of ref document: AT

Kind code of ref document: T

Effective date: 20181031

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: AT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190228

Ref country code: LV

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: NO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190131

Ref country code: LT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: PL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: HR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: BG

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190131

Ref country code: ES

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: PT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190301

Ref country code: RS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190201

Ref country code: AL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

REG Reference to a national code

Ref country code: DE

Ref legal event code: R097

Ref document number: 602012052835

Country of ref document: DE

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: MC

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

Ref country code: SM

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20190127

26N No opposition filed

Effective date: 20190801

REG Reference to a national code

Ref country code: BE

Ref legal event code: MM

Effective date: 20190131

REG Reference to a national code

Ref country code: IE

Ref legal event code: MM4A

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20190131

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20190131

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20190131

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20190127

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: TR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20200129

Year of fee payment: 9

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20190127

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20200128

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20200327

Year of fee payment: 9

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CY

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: HU

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT; INVALID AB INITIO

Effective date: 20120127

REG Reference to a national code

Ref country code: DE

Ref legal event code: R119

Ref document number: 602012052835

Country of ref document: DE

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20210127

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20210131

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20210127

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20210803

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20181031